Novel composition of matter for use in organic light-emitting diodes

ABSTRACT

The present disclosure relates to compounds of Formula (I) as useful materials for OLED&#39;s. X is C(R) 2 , O, S or —N(Ph); at least one of A 1  and A 2  is CN, cyanoaryl, or heteroaryl having at least one nitrogen atom as a ring-constituting atom; and at least one of D 1 , D 2 , D 3  and D 4  is diarylamino.

RELATED APPLICATIONS

This application claims the benefit of priority to U.S. ProvisionalPatent Application Ser. No. 62/727,752, filed Sep. 6, 2018, which ishereby expressly incorporated by reference, in its entirety, into thepresent application.

BACKGROUND

An organic light emitting diode (OLED) is a light-emitting diode (LED)in which a film of organic compounds is placed between two conductors,which film emits light in response to excitation, such as an electriccurrent. OLEDs are useful in displays, such as television screens,computer monitors, mobile phones, and tablets. A problem inherent inOLED displays is the limited lifetime of the organic compounds. OLEDswhich emit blue light, in particular, degrade at a significantlyincreased rate as compared to green or red OLEDs.

OLED materials rely on the radiative decay of molecular excited states(excitions) generated by recombination of electrons and holes in a hosttransport material. The nature of excitation results in interactionsbetween electrons and holes that split the excited states into brightsinglets (with a total spin of 0) and dark triplets (with a total spinof 1). Since the recombination of electrons and holes affords astatistical mixture of four spin states (one singlet and three tripletsublevels), conventional OLEDs have a maximum theoretical efficiency of25%.

To date, OLED material design has focused on harvesting the remainingenergy from the normally dark triplets. Recent work to create efficientphosphors, which emit light from the normally dark triplet state, haveresulted in green and red OLEDs. Other colors, such as blue, however,require higher energy excited states which accelerate the degradationprocess of the OLED.

The fundamental limiting factor to the triplet-singlet transition rateis a value of the parameter |H_(fi)/Δ|², where H_(fi) is the couplingenergy due to hyperfine or spin-orbit interactions, and Δ is theenergetic splitting between singlet and triplet states. Traditionalphosphorescent OLEDs rely on the mixing of singlet and triplet statesdue to spin-orbital (SO) interaction, increasing H_(fi), and affording alowest emissive state shared between a heavy metal atom and an organicligand. This results in energy harvesting from all higher singlet andtriplet states, followed by phosphorescence (relatively short-livedemission from the excited triplet). The shortened triplet lifetimereduces triplet exciton annihilation by charges and other excitons.Recent work by others suggests that the limit to the performance ofphosphorescent materials has been reached.

SUMMARY

The present disclosure relates to novel materials for OLEDs. These OLEDscan reach higher excitation states without rapid degradation. It has nowbeen discovered that thermally activated delayed fluorescence (TADF),which relies on minimization of Δ as opposed to maximization of H_(fi),can transfer population between singlet levels and triplet sublevels ina relevant timescale, such as, for example, 1-100 μs. The compoundsdescribed herein are capable of luminescing at higher energy excitationstates than compounds previously described.

In one aspect, the present disclosure provides:

[1] A compound of Formula (I):

wherein:

X is C(R)₂, O, S or —N(Ph),

R is independently selected from H, CH₃, and Ph;

Ph is substituted or unsubstituted phenyl,

one of A¹ and A² is AA,

AA is selected from CN, substituted or unsubstituted aryl having atleast one cyano, and substituted or unsubstituted heteroaryl having atleast one nitrogen atom as a ring-constituting atom,

the other of A¹ and A² is H, AA, substituted or unsubstituted alkyl, orsubstituted or unsubstituted aryl not having cyano,one of D¹, D², D³ and D⁴ is DD,

DD is represented by Formula (II):

R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are independently selected fromhydrogen, deuterium, substituted or unsubstituted alkyl, substituted orunsubstituted alkoxy, substituted or unsubstituted amino, substituted orunsubstituted aryl, substituted or unsubstituted aryloxy, substituted orunsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy,and silyl; or two or more instances of R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸taken together can form a ring system, or R⁵ and R⁶ taken together canform single bond,

L¹ is selected from single bond, substituted r unsubstituted arytene,and substituted or unsubstituted heteroarylene;

the others of D¹, D², D³ and D⁴ are selected from H, DD, substituted orunsubstituted alkyl, substituted or unsubstituted aryl other thanFormula (II).

[2] The compound of [1], wherein X is O.

[3] The compound of [1], wherein X is S.

[4] The compound of [1], wherein X is N(Ph).

[5] The compound of any one of [1] to [4], wherein DD has two carbazolerings.

[6] The compound of any one of [1] to [5], wherein at least one of D¹,D² and D⁴ is DD.

[7] The compound of any one of [1] to [5], wherein at least two of D¹,D², D³ and D⁴ are DD.

[8] The compound of any one of [1] to [7], wherein the at least two ofD¹, D², D³ and D⁴ are different from each other.

[9] The compound of any one of [1] to [8], wherein R⁵ and R⁶ takentogether form single bond, and R⁷ and R⁸ are not taken together.

[10] The compound of any one of [1] to [9], wherein at least one of D¹,D² and D⁴ is deuterium, substituted or unsubstituted alkyl, substitutedor unsubstituted alkoxy, substituted or unsubstituted amino, substitutedor unsubstituted aryl, substituted or unsubstituted aryloxy, substitutedor unsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy,or silyl.

[11] The compound of any one of [1] to [9], wherein at least one of D¹,D² and D⁴ is substituted or unsubstituted amino, or substituted orunsubstituted heteroaryl,

[12] The compound of any one of [1] to [11], wherein L¹ is substitutedor unsubstituted arylene, and substituted or unsubstitutedheteroarylene; wherein each instance of arylene and heteroarylene can besubstituted with one or more substituents independently selected fromdeuterium, substituted or unsubstituted alkyl, substituted orunsubstituted aryl, or substituted or unsubstituted heteroaryl.

[13] The compound of any one of [1] to [12], wherein A¹ and A² are thesame.

[14] The compound of any one of [1] to [12], wherein A¹ and A² are AAand different from each other.

[15] The compound of any one of [1] to [14], wherein at least one of A¹and A² is substituted or unsubstituted aryl having at least one cyano.

In one aspect, the present disclosure provides:

[16] An organic light-emitting diode (OLED) comprising the compound ofany one of [1] to [15].

The organic light-emitting diode (OLED) of [16], comprising an anode, acathode, and at least one organic layer comprising a light-emittinglayer between the anode and the cathode, wherein the light-emittinglayer comprises a host material and the compound.

[18] The organic light-emitting diode (OLED) of [16], comprising ananode, a cathode, and at least one organic layer comprising alight-emitting layer between the anode and the cathode, wherein thelight-emitting layer comprises the compound and a light-emittingmaterial, and light emission of the OLED occurs mainly in thelight-emitting material.

[19] The organic light-emitting diode (OLED) of [16], comprising ananode, a cathode, and at least one organic layer comprising alight-emitting layer between the anode and the cathode, wherein thelight-emitting layer comprises a host material, an assistant dopant anda light-emitting material, and the assistant dopant is the compound.

In one aspect, the present disclosure provides:

[20] A screen or a display comprising the compound of any one of [1] to[15].

BRIEF DESCRIPTION OF THE DRAWING

FIG. 1 is a schematic wherein 1 denotes a substrate, 2 denotes an anode,3 denotes a hole injection layer, 4 denotes a hole transporting layer, 5denotes a light-emitting layer, 6 denotes an electron transportinglayer, and 7 denotes a cathode.

DETAILED DESCRIPTION

The examples are provided by way of explanation of the disclosure, andnot by way of limitation of the disclosure. In fact, it will be apparentto those skilled in the art that various modification and variations canbe made in the present disclosure without departing from the scope orspirit of the disclosure. For instance, features illustrated ordescribed as part of one embodiment can be used on another embodiment toyield a still further embodiment. Thus, it is intended that the presentdisclosure cover such modifications and variations as come within thescope of the appended claims and their equivalents. Other objects,features, and aspects of the present disclosure are disclosed in, or canbe derived from, the following detailed description. It is to beunderstood by one of ordinary skill in the art that the presentdiscussion is a description of exemplary embodiments only, and is not tobe construed as limiting the broader aspects of the present disclosure.

Definitions

Unless otherwise defined herein, scientific and technical terms used inthis application shall have the meanings that are commonly understood bythose of ordinary skill in the art. Generally, nomenclature used inconnection with, and techniques of, chemistry described herein, arethose well-known and commonly used in the art.

The term “acyl” is art-recognized and refers to a group represented bythe general formula hydrocarbylC(O)—, preferably alkylC(O)—.

The term “acylamino” is art-recognized and refers to an amino groupsubstituted with an acyl group and may be represented, for example, bythe formula hydrocarbylC(O)NH—.

The term “acyloxy” is art-recognized and refers to a group representedby the general formula hydrocarbylC(O)O—, preferably alkylC(O)O—.

The term “alkoxy” refers to an alkyl group, having an oxygen attachedthereto. In some embodiments, an alkoxy has 1-20 carbon atoms. In someembodiments, an alkoxy has 1-12 carbon atoms. Representative alkoxygroups include methoxy, trifluoromethoxy, ethoxy, propoxy, tert-butoxyand the like.

The term “alkoxyalkyl” refers to an alkyl group substituted with analkoxy group and may be represented by the general formulaalkyl-O-alkyl.

The term “alkenyl”, as used herein, refers to an aliphatic groupcomprising at least one double bond and is intended to include both“unsubstituted alkenyls” and “substituted alkenyls”, the latter of whichrefers to alkenyl moieties having substituents replacing a hydrogen onone or more carbons of the alkenyl group. Typically, a straight chainedor branched alkenyl group has from 1 to about 20 carbon atoms,preferably from 1 to about 12 unless otherwise defined. Suchsubstituents may occur on one or more carbons that are included or notincluded in one or more double bonds. Moreover, such substituentsinclude all those contemplated for alkyl groups, as discussed below,except where stability is prohibitive. For example, substitution ofalkenyl groups by one or more alkyl, carbocyclyl, aryl, heterocyclyl, orheteroaryl, groups is contemplated.

An “alkyl” group or “alkane” is a straight chained or branchednon-aromatic hydrocarbon which is completely saturated. Typically, astraight chained or branched alkyl group has from 1 to about 20 carbonatoms, preferably from 1 to about 12 unless otherwise defined. In someembodiments, the alkyl group has from 1 to 8 carbon atoms, from 1 to 6carbon atoms, from 1 to 4 carbon atoms, or from 1 to 3 carbon atoms.Examples of straight chained and branched alkyl groups include methyl,ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, pentyl,hexyl, pentyl and octyl.

Moreover, the term “alkyl” as used throughout the specification,examples, and claims is intended to include both “unsubstituted alkyls”and “substituted alkyls”, the latter of which refers to alkyl moietieshaving substituents replacing a hydrogen on one or more substitutablecarbons of the hydrocarbon backbone. Such substituents, if not otherwisespecified, can include, for example, a halogen (e.g., fluoro), ahydroxyl, a carbonyl (such as a carboxyl, an alkoxycarbonyl, a formyl,or an acyl), a thiocarbonyl (such as a thioester, a thioacetate, or athioformate), an alkoxy, a phosphoryl, a phosphate, a phosphonate, aphosphinate, an amino, an amido, an amidine, an imine, a cyano, a nitro,an azido, sulfhydryl, an alkylthio, a sulfate, a sulfonate, a sulfhmoyl,a sulfonamido, a sulfonyl, a heterocyclyl, an aralkyl, or an aromatic orheteroaromatic moiety. In preferred embodiments, the substituents onsubstituted alkyls are selected from C₁₋₆ alkyl, C₃₋₆ cycloalkyl,halogen, carbonyl, cyano, or hydroxyl. In more preferred embodiments,the substituents on substituted alkyls are selected from fluoro,carbonyl, cyano, or hydroxyl. It will be understood by those skilled inthe art that the moieties substituted on the hydrocarbon chain canthemselves be substituted, if appropriate. For instance, thesubstituents of a substituted alkyl may include substituted andunsubstittited forms of amino, azido, imino, amido, phosphoryl(including phosphonate and phosphinate), sulfonyl (including sulfate,sulfonamido, sulfamoyl and sulfonate), and silyl groups, as well asethers, alkyithios, carbonyls (including ketones, aldehydes,carboxylates, and esters), —CF₃, —CN and the like. Exemplary substitutedalkyls are described below. Cycloalkyls can be further substituted withalkyls, alkenyls, alkoxys, alkylthios, aminoalkyls, carbonyl-substitutedalkyls, —CF₃, —CN, and the like.

The term “C_(x-y)” when used in conjunction with a chemical moiety, suchas, acyl, acyloxy, alkyl, alkenyl, alkynyl, or alkoxy is meant toinclude groups that contain from x to y carbons in the chain. Forexample, the term “C_(x-y) alkyl” refers to substituted or unsubstitutedsaturated hydrocarbon groups, including straight-chain alkyl andbranched-chain alkyl groups that contain from x to y carbons in thechain, including haloalkyl groups. Preferred haloalkyl groups includetrifluoromethyl, difluoromethyl, 2,2,2-trifluoroethyl, andpentafluoroethyl. C₀ alkyl indicates a hydrogen where the group is in aterminal position, a bond if internal. The terms “C_(2-y) alkenyl” and“C_(2-y) alkynyl” refer to substituted or unsubstituted unsaturatedaliphatic groups analogous in length and possible substitution to thealkyls described above, but that contain at least one double or triplebond respectively.

The term “alkylamino”, as used herein, refers to an amino groupsubstituted with at least one alkyl group.

The term “alkylthio”, as used herein, refers to a thiol groupsubstituted with an alkyl group and may be represented by the generalformula alkylS—.

The term “arylthio”, as used herein, refers to a thiol group substitutedwith an alkyl group and may be represented by the general formulaarylS—.

The term “alkynyl”, as used herein, refers to an aliphatic groupcomprising at least one triple bond and is intended to include both“unsubstituted alkynyls” and “substituted alkynyls”, the latter of whichrefers to alkynyl moieties having substituents replacing a hydrogen onone or more carbons of the alkynyl group. Typically, a straight chainedor branched alkynyl group has from 1 to about 20 carbon atoms,preferably from 1 to about 10 unless otherwise defined. Suchsubstituents may occur on one or more carbons that are included or notincluded in one or more triple bonds. Moreover, such substituentsinclude all those contemplated for alkyl groups, as discussed above,except where stability is prohibitive. For example, substitution ofalkynyl groups by one or more alkyl, carbocyclyl, aryl, heterocyclyl, orheteroaryl groups is contemplated.

The term “amide”, as used herein, refers to a group

wherein each R^(A) independently represents a hydrogen or hydrocarbylgroup, or two R^(A) are taken together with the N atom to which they areattached complete a heterocycle having from 4 to 8 atoms in the ringstructure.

The terms “amine” and “amino” are art-recognized and refer to bothunsubstituted and substituted amines and salts thereof, e.g., a moietythat can be represented by

wherein each R^(A) independently represents a hydrogen or a hydrocarbylgroup, or two R^(A) are taken together with the N atom to which they areattached complete a heterocycle having from 4 to 8 atoms in the ringstructure.

The term “aminoalkyl”, as used herein, refers to an alkyl groupsubstituted with an amino group.

The term “aralkyl”, as used herein, refers to an alkyl group substitutedwith an aryl group.

The term “aryl” as used herein include substituted or unsubstitutedsingle-ring aromatic groups in which each atom of the ring is carbon.Preferably the ring is a 6- or 20-membered ring, more preferably a6-membered ring, Preferably aryl having 6-40 carbon atoms, morepreferably having 6-25 carbon atoms.

The term “aryl” also includes polycyclic ring systems having two or morecyclic rings in which two or more carbons are common to two adjoiningrings wherein at least one of the rings is aromatic, e.g., the othercyclic rings can be cycloalkyls, cycloalkenyls, cycloalkynyls, aryls,heteroaryls, and/or heterocyclyls. Aryl groups include benzene,naphthalene, phenanthrene, phenol, aniline, and the like.

The term “carbamate” is art-recognized and refers to a group

wherein each R^(A) independently represent hydrogen or a hydrocarbylgroup, such as an alkyl group, or both R^(A) taken together with theintervening atom(s) complete a heterocycle having from 4 to 8 atoms inthe ring structure.

The terms “carbocycle”, and “carbocyclic”, as used herein, refers to asaturated or unsaturated ring in which each atom of the ring is carbon.Preferably, a carbocylic group has from 3 to 20 carbon atoms. The termcarbocycle includes both aromatic carbocycles and non-aromaticcarbocycles. Non-aromatic carbocycles include both cycloalkane rings, inwhich all carbon atoms are saturated, and cycloalkane rings, whichcontain at least one double bond. “Carbocycle” includes 5-7 memberedmonocyclic and 8-12 membered bicyclic rings. Each ring of a bicycliccarbocycle may be selected from saturated, unsaturated and aromaticrings. Carbocycle includes bicyclic molecules in which one, two or threeor more atoms are shared between the two rings. The term “fusedcarbocycle” refers to a bicyclic carbocycle in which each of the ringsshares two adjacent atoms with the other ring. Each ring of a fusedcarbocycle may be selected from saturated, unsaturated and aromaticrings. In an exemplary embodiment, an aromatic ring, e.g., phenyl (Ph),may be fused to a saturated or unsaturated ring, e.g., cyclohexane,cyclopentane, or cyclohexene. Any combination of saturated, unsaturatedand aromatic bicyclic rings, as valence permits, is included in thedefinition of carbocyclic. Exemplary “carbocycles” include cyclopentane,cyclohexane, bicyclo[2.2.1]heptane, 1,5-cyclooctadiene,1,2,3,4-tetrahydronaphthalene, bicyclo[4.2.0]oct-3-ene, naphthalene andadamantane. Exemplary fused carbocycles include decalin, naphthalene,1,2,3,4-tetrahydronaphthalene, bicyclo[4.2.0]octane,4,5,6,7-tetrahydro-1H-indene and bicyclo[4.1.0]hept-3-ene, “Carbocycles”may be substituted at any one or more positions capable of bearing ahydrogen atom.

A “cycloalkyl” group is a cyclic hydrocarbon which is completelysaturated. “Cycloalkyl” includes monocyclic and bicyclic rings.Preferably, a cycloalkyl group has from 3 to 20 carbon atoms. Typically,a monocyclic cycloalkyl group has from 3 to about 10 carbon atoms, moretypically 3 to 8 carbon atoms unless otherwise defined. The second ringof a bicyclic cycloalkyl may be selected from saturated, unsaturated andaromatic rings. Cycloalkyl includes bicyclic molecules in which one, twoor three or more atoms are shared between the two rings. The term “fusedcycloalkyl” refers to a bicyclic cycloalkyl in which each of the ringsshares two adjacent atoms with the other ring. The second ring of afused bicyclic cycloalkyl may be selected from saturated, unsaturatedand aromatic rings. A “cycloalkenyl” group is a cyclic hydrocarboncomprising one or more double bonds.

The term “carbocyclyalkyl,” as used herein, refers to an alkyl groupsubstituted with a carbocycle group.

The term “carbonate,” as used herein, refers to a group —OCO₂—R^(A),wherein R^(A) represents a hydrocarbyl group.

The term “carboxy,” as used herein, refers to a group represented by theformula —CO₂H.

The term “ester,” as used herein, refers to a group —C(O)OR^(A) whereinR^(A) represents a hydrocarbyl group.

The term “ether,” as used herein, refers to a hydrocarbyl group linkedthrough an oxygen to another hydrocarbyl group, Accordingly, an ethersubstituent of a hydrocarbyl group may be hydrocarbyl-O—. Ethers may beeither symmetrical or unsymmetrical.

Examples of ethers include, but are not limited to,heterocycle-O-heterocycle and aryl-O-heterocycle. Ethers include“alkoxyalkyl” groups, which may be represented by the general formulaalkyl-O-alkyl.

The terms “halo” and “halogen” as used herein means halogen and includeschloro, fluoro, bromo, and iodo.

The terms “hetaralkyl” and “heteroaralkyl,” as used herein, refers to analkyl group substituted with a hetaryl group.

The term “heteroalkyl,” as used herein, refers to a saturated orunsaturated chain of carbon atoms and at least one heteroatom, whereinno two heteroatoms are adjacent. The terms “heteroaryl” and “hetaryl”include substituted or unsubstituted aromatic single ring structures,preferably 5- to 20-membered rings, more preferably 5- to 6-memberedrings, whose ring structures include at least one heteroatom, preferablyone to four heteroatoms, more preferably one or two heteroatoms.Preferably a heteroaryl having 2-40 carbon atoms, more preferably having2-25 carbon atoms. The terms “heteroaryl” and “hetaryl” also includepolycyclic ring systems having two or more cyclic rings in which two ormore carbons are common to two adjoining rings wherein at least one ofthe rings is heteroaromatic, e.g., the other cyclic rings can becycloalkyls, cycloalkenyls, cycloalkynyis, aegis, heteroaryls, and/orheterocyclyls. Heteroaryl groups include, for example, pyrrole, furan,thiophene, imidazole, oxazole, thiazole, pyrazole, pyridine, pyrazine,pyridazine, pyrimidine, and carbazole, and the like.

The term “aryloxy” refers to an aryl group, having an oxygen attachedthereto. Preferably aryloxy having 6-40 carbon atoms, more preferablyhaving 6-25 carbon atoms.

The term “heteroaryloxy” refers to an aryl group, having an oxygenattached thereto. Preferably heteroaryloxy having 3-40 carbon atoms,more preferably having 3-25 carbon atoms.

The term “heteroatom” as used herein means an atom of any element otherthan carbon or hydrogen. Preferred heteroatoms are nitrogen, oxygen, andsulfur.

The terms “heterocyclyl,” “heterocycle,” and “heterocyclic” refer tosubstituted or unsubstituted non-aromatic ring structures, preferably 3-to 20-membered rings, more preferably 3- to 7-membered rings, whose ringstructures include at least one heteroatom, preferably one to fourheteroatoms, more preferably one or two heteroatoms. The terms“heterocyclyl” and “heterocyclic” also include polycyclic ring systemshaving two or more cyclic rings in which two or more carbons are commonto two adjoining rings wherein at least one of the rings isheterocyclic, e.g., the other cyclic rings can be cycloalkyls,cycloalkenyls, cycloalkynyls, aryls, heteroaryls, and/or heterocyclyls.Heterocyclyl groups include, for example, piperidine, piperazine,pyrrolidine, morpholine, lactones, lactams, and the like.

The term “heterocyclylalkyl,” as used herein, refers to an alkyl groupsubstituted with a heterocycle group.

The term “hydrocarbyl,” as used herein, refers to a group that is bondedthrough a carbon atom, wherein that carbon atom does not have a ═O or ═Ssubstituent. Hydrocarbyls may optionally include heteroatoms.Hydrocarbyl groups include, but are not limited to, alkyl, alkenyl,alkynyl, alkoxyalkyl, arninoalkyl, aralkyl, aryl, aralkyl, carbocyclyl,cycloalkyl, carbocyclylalkyl, heteroaralkyl, heteroaryl groups bondedthrough a carbon atom, heterocyclyl groups bonded through a carbon atom,heterocyclylakyl, or hydroxyalkyl. Thus, groups like methyl,ethoxyethyl, 2-pyridyl, and trifluoromethyl are hydrocarbyl groups, butsubstituents such as acetyl (which has a ═O substituent on the linkingcarbon) and ethoxy (which is linked through oxygen, not carbon) are not.

The term “hydroxyalkyl,” as used herein, refers to an alkyl groupsubstituted with a hydroxy group.

The term “lower” when used in conjunction with a chemical moiety, suchas, aryl, acyloxy, alkyl, alkenyl, alkynyl, or alkoxy is meant toinclude groups where there are six or fewer non-hydrogen atoms in thesubstituent. A “lower alkyl,” for example, refers to an alkyl group thatcontains six or fewer carbon atoms. In some embodiments, the alkyl grouphas from 1 to 6 carbon atoms, from 1 to 4 carbon atoms, or from 1 to 3carbon atoms. In certain embodiments, acyl, acyloxy, alkyl, alkenyl,alkynyl, or alkoxy substituents defined herein are respectively loweracyl, lower acyloxy, lower alkyl, lower alkenyl, lower alkynyl, or loweralkoxy, whether they appear alone or in combination with othersubstituents, such as in the recitations hydroxyalkyl and aralkyl (inwhich ease, for example, the atoms within the aryl group are not countedwhen counting the carbon atoms in the alkyl substituent).

The terms “polycyclyl,” “polycycle”, and “polycyclic” refer to two ormore rings (e.g., cycloalkyls, cycloalkenyls, cycloalkynyls, aryls,heteroaryls, and/or heterocyclyls) in which two or more atoms are commonto two adjoining rings, e.g., the rings are “fused rings”. Each of therings of the polycycle can he substituted or unsubstituted. In certainembodiments, each ring of the polycycle contains from 3 to 10 atoms inthe ring, preferably from 5 to 7.

In the phrase “poly(meta-phenylene oxides),” the term “phenylene” refersinclusively to 6-membered aryl or 6-membered heteroaryl moieties.Exemplary poly(meta-phenylene oxides) are described in the first throughtwentieth aspects of the present disclosure.

The term “silyl” refers to a silicon moiety with three hydrocarbylmoieties attached thereto.

The term “substituted” refers to moieties having substituents replacinga hydrogen on one or more carbons of the backbone. It will be understoodthat “substitution” or “substituted with” includes the implicit provisothat such substitution is in accordance with permitted valence of thesubstituted atom and the substituent, and that the substitution resultsin a stable compound, e.g., which does not spontaneously undergotransformation such as by rearrangement, cyclization, elimination, etc.Moieties that may be substituted can include any appropriatesubstituents described herein, for example, acyl, acylamino, acyloxy,alkoxy, alkoxyalkyl, alkenyl, alkyl, alkylthio, arylthio, alkynyl,amide, amino, aminoalkyl, aralkyl, carbamate, carbocyclyl, cycloalkyl,carbocyclylalkyl, carbonate, ester, ether, heteroaralkyl, heterocyclyl,heterocyclylalkyl, hydrocarbyl, silyl, sulfone, or thioether. As usedherein, the term “substituted” is contemplated to include allpermissible substituents of organic compounds. In a broad aspect, thepermissible substituents include acyclic and cyclic, branched andunbranched, carbocyclic and heterocyclic, aromatic and non-aromaticsubstituents of organic compounds. The permissible substituents can beone or more and the same or different for appropriate organic compounds.For purposes of this invention, the heteroatoms such as nitrogen mayhave hydrogen substituents and/or any permissible substituents oforganic compounds described herein which satisfy the valences of theheteroatoms. Substituents can include any substituents described herein,for example, a halogen, a hydroxyl, a carbonyl (such as a carboxyl, analkoxycarbouyl, a formyl, or an acyl), a thiocarbonyl (such as athioester, a thioacetate, or a thioformate), an alkoxy, a phosphoryl, aphosphate, a phosphonate, phosphinate, an amino, an amino, an amidine,an imine, a cyano, a nitro, an azido, a sulthydryl, an alkylthio, asulfate, a sulfonate, a sulfamoyl, a sulfonamido, a sulfonyl, aheterocyclyl, an aralkyl, or an aromatic or heteroaromatic moiety. Inpreferred embodiments, the substituents on substituted alkyls areselected from C₁₋₆ alkyl, C₃₋₆ cycloalkyl, halogen, carbonyl, cyano, orhydroxyl. In more preferred embodiments, the substituents on substitutedalkyls are selected from fluoro, carbonyl, cyano, or hydroxyl. It willbe understood by those skilled in the art that substituents canthemselves be substituted, if appropriate. Unless specifically stated as“unsubstituted,” references to chemical moieties herein are understoodto include substituted variants. For example, reference to an “aryl”group or moiety implicitly includes both substituted and unsubstitutedvariants.

The term “sulfonate” is art-recognized and refers to the group SO₃H, ora pharmaceutically acceptable salt thereof.

The term “sulfone” is art-recognized and refers to the group—S(O)—R^(A), wherein R^(A) represents a hydrocarbyl.

The term “thioether,” as used herein, is equivalent to an ether, whereinthe oxygen is replaced with a sulfur.

The term “symmetrical molecule,” as used herein, refers to moleculesthat are group symmetric or synthetic symmetric. The term “groupsymmetric,” as used herein, refers to molecules that have symmetryaccording to the group theory of molecular symmetry. The term “syntheticsymmetric,” as used herein, refers to molecules that are selected suchthat no regioselective synthetic strategy is required.

The term “donor,” as used herein, refers to a molecular fragment thatcan be used in organic light emitting diodes and is likely to donateelectrons from its highest occupied molecular orbital to an acceptorupon excitation. In preferred embodiments, donor contain substitutedamino group. In an example embodiment, donors have an ionizationpotential greater than or equal to −6.5 eV. The term “acceptor,” as usedherein, refers to a molecular fragment that can be used in organic lightemitting diodes and is likely to accept electrons into its lowestunoccupied molecular orbital from a donor that has been subject toexcitation. In an example embodiment, acceptors have an electronaffinity less than or equal to −0.5 eV.

The term “bridge,” as used herein, refers to a molecular fragment thatcan be included in a molecule which is covalently linked betweenacceptor and donor moieties. The bridge can, for example, he furtherconjugated to the acceptor moiety, the donor moiety, or both. Withoutbeing bound to any particular theory, it is believed that the bridgemoiety can sterically restrict the acceptor and donor moieties into aspecific configuration, thereby preventing the overlap between theconjugated π system of donor and acceptor moieties. Examples of suitablebridge moieties include phenyl, ethenyl, and ethynyl.

The terms “multivalent,” as used herein, refers to a molecular fragmentthat is connected to at least two other molecular fragments. Forexample, a bridge moiety, is multivalent.

“

” or “*” as used herein, refers to a point of attachment between twoatoms.

“Hole transport layer (HTL)” and like terms mean a layer made from amaterial which transports holes. High hole mobility is recommended. TheHTL is used to help block passage of electrons transported by theemitting layer. Low electron affinity is typically required to blockelectrons. The HTL should desirably have larger triplets to blockexciton migrations from an adjacent emissive layer (EML). Examples ofHTL compounds include, but are not limited to,di(p-tolyl)aminophenyl]cyclohexane (TAPC),N,N-diphenyl-N,N-bis(3-methylphenyl)-1,1-biphenyl-4,4-diamine (TPD), andN,N′-diphenyl-N,N′-bis(1-naphthyl)-(1,1′-biphenyl)-4,4′-diamine (NPB,α-NPD).

“Emitting layer” and like terms mean a layer which emits light. In someembodiments, the emitting layer comprises a host material and guestmaterial. The guest material can also be referred to as a dopantmaterial, but the disclosure is not limited thereto. The host materialcould be bipolar or unipolar and may be used alone or by combination oftwo or more host materials. The opto-electrical properties of the hostmaterial may differ to which type of guest material (TADF,Phosphorescent or Fluorescent) is used. For Fluorescent guest materials,the host materials should have good spectral overlap between absorptionof the guest material and emission of the host material to induce goodForster transfer to guest materials. For Phosphorescent guest materials,the host materials should have high triplet energy to confine tripletsof the guest material. For TADF guest materials, the host materialsshould have both spectral overlap and higher triplet energy.

“Dopant” and like terms, refer to additive materials for carriertransporting layers, emitting layers or other layers. In carriertransporting layers, dopant and like terms perform as an electronacceptor or a donator that increases the conductivity of an organiclayer of an organic electronic device, when added to the organic layeras an additive. Organic semiconductors may likewise be influenced, withregard to their electrical conductivity, by doping. Such organicsemiconducting matrix materials may be made up either of compounds withelectron-donor properties or of compounds with electron-acceptorproperties. In emitting layers, dopant and like terms also mean thelight emitting material which is dispersed in a matrix, for example, ahost. When a triplet harvesting material is doped into an emitting layeror contained in an adjacent layer so as to improve exciton generationefficiency, it is named as assistant dopant. An assistant dopant maypreferably shorten a lifetime of the exciton. The content of theassistant dopant in the light emitting layer or the adjacent layer isnot particularly limited so long as the triplet harvesting materialimproves the exciton generation efficiency. The content of the assistantdopant in the light emitting layer is preferably higher than, morepreferably at least twice than the light emitting material. In the lightemitting layer, the content of the host material is preferably 50% byweight or more, the content of the assistant dopant is preferably from5% by weight to less than 50% by weight, and the content of the lightemitting material is preferably more than 0% by weight to less than 30%by weight, more preferably from 0% by weight to less than 10% by weight.The content of the assistant dopant in the adjacent layer may be morethan 50% by weight and may be 100% by weight. In the case where a devicecomprising a triplet harvesting material in a light emitting layer or anadjacent layer has a higher light emission efficiency than a devicewithout the triplet harvesting material, such triplet harvestingmaterial functions as an assistant dopant. A light emitting layercomprising a host material, an assistant dopant and a light emittingmaterial satisfies the following (A) and preferably satisfies thefollowing (B):

ES1(A)>ES1(B)>ES1(C)  (A)

ET1(A)>ET1(B)  (B)

wherein ES1(A) represents a lowest excited singlet energy level of thehost material; ES1(B) represents a lowest excited singlet energy levelof the assistant dopant; ES1(C) represents a lowest excited singletenergy level of the light emitting material; ET1(A) represents a lowestexcited triplet energy level at 77 K of the host material; and ET1(B)represents a lowest excited triplet energy level at 77 K of theassistant dopant. The assistant dopant has an energy difference ΔE_(ST)between a lowest singlet excited state and a lowest triplet excitedstate at 77 K of preferably 0.3 eV or less, more preferably 0.2 eV orless, still more preferably 0.1 eV or less.

In the compounds of this invention any atom not specifically designatedas a particular isotope is meant to represent any stable isotope of thatatom. Unless otherwise stated, when a position is designatedspecifically as “H” or “hydrogen”, the position is understood to havehydrogen at its natural abundance isotopic composition. Also, unlessotherwise stated, when a position is designated specifically as “d” or“deuterium”, the position is understood to have deuterium at anabundance that is at least 3340 times greater than the natural abundanceof deuterium, which is 0.015% (i.e., at least 50.1% incorporation ofdeuterium).

The term “isotopic enrichment factor” as used herein means the ratiobetween the isotopic abundance and the natural abundance of a specifiedisotope.

In various embodiments, compounds of this invention have an isotopicenrichment factor for each designated deuterium atom of at least 3500(52.5% deuterium incorporation at each designated deuterium atom), atleast 4000 (60% deuterium incorporation), at least 4500 (67.5% deuteriumincorporation), at least 5000 (75% deuterium), at least 5500 (82.5%deuterium incorporation), at least 6000 (90% deuterium incorporation),at least 6333.3 (95% deuterium incorporation), at least 6466.7 (97%deuterium incorporation), at least 6600 (99% deuterium incorporation),or at leak 6633.3 (99.5% deuterium incorporation).

The term “isotopologue” refers to a species that differs from a specificcompound of this invention only in the isotopic composition thereof.

The term “compound,” when referring to a compound of this invention,refers to a collection of molecules having an identical chemicalstructure, except that there may he isotopic variation among theconstituent atoms of the molecules. Thus, it will be clear to those ofskill in the art that a compound represented by a particular chemicalstructure containing indicated deuterium atoms, will also contain lesseramounts of isotopologues having hydrogen atoms at one or more of thedesignated deuterium positions in that structure. The relative amount ofsuch isotopologues in a compound of this invention will depend upon anumber of factors including the isotopic purity of deuterated reagentsused to make the compound and the efficiency of incorporation ofdeuterium in the various synthesis steps used to prepare the compound.However, as set forth above the relative amount of such isotopologues intote will be less than 49.9% of the compound. In other embodiments, therelative amount of such isotopologues in tote will be less than 47.5%,less than 40%, less than 32.5%, less than 25%, less than 17.5%, lessthan 10%, less than 5%, less than 3%, less than 1%, or less than 0.5% ofthe compound.

“Substituted with deuterium” refers to the replacement of one or morehydrogen atoms with a corresponding number of deuterium atoms. “D” and“d” both refer to deuterium.

Principles of OLED

OLEDs are typically composed of a layer of organic materials orcompounds between two electrodes, an anode and a cathode. The organicmolecules are electrically conductive as a result of delocalization of πelectronics caused by conjugation over part or all of the molecule. Whenvoltage is applied, electrons from the highest occupied molecularorbital (HOMO) present at the anode flow into the lowest unoccupiedmolecular orbital (LUMO) of the organic molecules present at thecathode. Removal of electrons from the HOMO is also referred to asinserting electron holes into the HOMO. Electrostatic forces bring theelectrons and the holes towards each other until they recombine and forman exciton (which is the bound state of the electron and the hole). Asthe excited state decays and the energy levels of the electrons relax,radiation having a frequency in the visible spectrum is emitted. Thefrequency of this radiation depends on the band gap of the material,which is the difference in energy between the HOMO and the LUMO.

As electrons and holes are fermions with half integer spin, an excitonmay either be in a singlet state or a triplet state depending on how thespins of the electron and hole have been combined. Statistically, threetriplet excitons will he formed for each singlet exciton. Decay fromtriplet states is spin forbidden, which results in increases in thetimescale of the transition and limits the internal efficiency offluorescent devices. Phosphorescent organic light-emitting diodes makeuse of spin-orbit interactions to facilitate intersystem crossingbetween singlet and triplet states, thus obtaining emission from bothsinglet and triplet states and improving the internal efficiency.

One prototypical phosphorescent material is iridiumtris(2-phenylpyridine (Ir(ppy)₃) in which the excited state is a chargetransfer from the Ir atom to the organic ligand. Such approaches havereduced the triplet lifetime to about several μs, several orders ofmagnitude slower than the radiative lifetimes of fully-allowedtransitions such as fluorescence. Ir-based phosphors have proven to beacceptable for many display applications, but losses due to largetriplet densities still prevent the application of OLEDs to solid-statelighting at higher brightness.

Thermally activated delayed fluorescence (TADF) seeks to minimizeenergetic splitting between singlet and triplet states (Δ, ΔE_(ST)). Thereduction in exchange splitting from typical values of 0.4-0.7 eV to agap of the order of the thermal energy (proportional to kBT, where kBrepresents the Boltzmann constant, and T represents temperature) meansthat thermal agitation can transfer population between singlet levelsand triplet levels in a relevant timescale even if the coupling betweenstates is small.

TADF molecules consist of donor and acceptor moieties connected directlyby a covalent bond or via a conjugated linker (or “bridge”). A “donor”moiety is likely to transfer electrons from its HOMO upon excitation tothe “acceptor” moiety. An “acceptor” moiety is likely to accept theelectrons from the “donor” moiety into its LUMO. The donor-acceptornature of TADF molecules results in low-lying excited states withcharge-transfer character that exhibit very low ΔE_(ST). Since thermalmolecular motions can randomly vary the optical properties ofdonor-acceptor systems, a rigid three-dimensional arrangement of donorand acceptor moieties can be used to limit the non-radiative decay ofthe charge-transfer state by internal conversion during the lifetime ofthe excitation.

It is beneficial, therefore, to decrease ΔE_(ST), and to create a systemwith increased reversed intersystem crossing (RISC) capable ofexploiting triplet excitons. Such a system, it is believed, will resultin increased quantum efficiency and decreased emission lifetimes.Systems with these features will be capable of emitting light withoutbeing subject to the rapid degradation prevalent in OLEDs known today.

Compounds of the Disclosure

In some embodiments, the compounds have a structure of Formula (I):

wherein

X is C(R)₂, O, S or —N(Ph),

R is independently selected from H, CH₃, and Ph;

Ph is substituted or unsubstituted phenyl;

one of A¹ and A² is AA,

AA is selected from CN, substituted or unsubstituted aryl having atleast one cyano, and substituted or unsubstituted heteroaryl having atleast one nitrogen atom as a ring-constituting atom,

the other of A¹ and A² is H, AA, substituted or unsubstituted alkyl, orsubstituted or unsubstituted aryl not having cyano;

one of D¹, D², D³ and D⁴ is DD,

DD is represented by Formula (II);

R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are independently selected fromhydrogen, deuterium, substituted or unsubstituted alkyl, substituted orunsubstituted alkoxy, substituted or unsubstituted amino, substituted orunsubstituted aryl, substituted or unsubstituted aryloxy, substituted orunsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy,and silyl; or two or more instances of R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸taken together can form a ring system, or R⁵ and R⁶ taken together canform single bond,

L¹ is selected from single bond, substituted or unsubstituted arylene,and substituted or unsubstituted heteroarylene;

the others of D¹, D², D³ and D⁴ are selected from H, DD, substituted orunsubstituted alkyl, substituted or unsubstituted aryl other thanFormula (II).

In some embodiments, alkyl is C1-C20-alkyl. In some embodiments, alkylis C1-C12 alkyl. In some embodiments, alkyl is C1-C6 alkyl. In someembodiments, alkyl is C1-C3 alkyl. In some embodiments, aryl is C6-C40aryl. In some embodiments, aryl is C6-C25 aryl. In some embodiments,aryl is C6-C14 aryl. In some embodiments, aryl is C6-C10 aryl. In someembodiments, heteroaryl is C2-C40 heteroaryl. In some embodiments,heteroaryl has 5-40 ring-constituting atoms. In some embodiments,heteroaryl has 5-25 ring-constituting atoms. In some embodiments,heteroaryl has 5-10 ring-constituting atoms. In some embodiments, alkoxyis C1-C20 alkoxy. In some embodiments, alkoxy is C1-C12 alkoxy. In someembodiments, alkoxy is C1-C6 alkoxy. In some embodiments, alkoxy isC1-C3 alkoxy. In some embodiments, aryloxy is C6-C40 aryloxy. In someembodiments, aryloxy is C6-C25 aryloxy. In some embodiments, aryloxy isC6-C14 aryloxy. In some embodiments, aryloxy is C6-C10 aryloxy. In someembodiments, heteroaryloxy is C3-C40 heteroaryloxy. In some embodiments,heteroaryloxy has 5-40 ring-constituting atoms. In some embodiments,heteroaryloxy has 5-25 ring-constituting atoms. In some embodiments,heteroaryloxy has 5-10 ring-constituting atoms.

In Formula (I), X is C(R)₂, O, S or N(Ph). In some embodiments, X isselected from CH₂, C(CH₃)₂, CH(CH₃), CH(C₆H₅), CH(C₆H₄-p-CH₃),CH(C₆H₄-m-CH₃), CH(C₆H₄-m,m-diCH₃), C(C₆H₅)₂, C(C₆H₄-p-CH₃)₂,C(C₆H₄-m-CH₃)₂, C(C₆H₄-m,m-diCH₃)₂, O, S, N(C₆H₅), N(C₆H₄-p-CH₃),N(C₆H₄-m-CH₃), and N(C₆H₄-m,m-diCH₃).

In Formula (I), one of A¹ and A² is AA; and the other of A¹ and A² is H,AA, substituted or unsubstituted alkyl, or substituted or unsubstitutedaryl not having cyano. In one embodiment, A¹ and A² are independentlyAA. In one embodiment, A¹ is AA, and A² is H. In one embodiment, A¹ isAA, and A² is substituted or unsubstituted alkyl. In one embodiment, A¹is AA, and A² is substituted or unsubstituted aryl not having cyano. Inone embodiment, A¹ is H, and A² is AA. In one embodiment, A¹ issubstituted or unsubstituted alkyl, and A² is AA. In one embodiment, A¹is substituted or unsubstituted aryl not having cyano, and A² is AA.

AA is selected from CN, substituted or unsubstituted aryl having atleast one cyano, and substituted or unsubstituted heteroaryl having atleast one nitrogen atom as a ring-constituting atom. When two AA's existin Formula (I), they may be the same or different. In some embodiments,two AA's are the same. In some embodiments, AA is CN. In someembodiments, AA is 4-cyanophenyl. In some embodiments, AA is3-cyanophenyl. In some embodiments, AA is substituted or unsubstitutedheteroaryl having at least one nitrogen atom as a ring-constitutingatom. In some embodiments, AA is substituted heteroaryl having at leastone nitrogen atom as a ring-constituting atom. In some embodiments, AAis aryl-substituted heteroaryl having at least one nitrogen atom as aring-constituting atom.

In some embodiments, AA is

In some embodiments, AA is

In some embodiments, AA is

In some embodiments, AA is

In some embodiments, AA is

In some embodiments, R¹¹, R¹², R¹³, R¹⁴ and R¹⁵ are independently H, CN,substituted or unsubstituted alkyl, substituted or unsubstituted aryl,or substituted or unsubstituted heteroaryl. Each instance of alkyl canbe substituted with one or more substituents independently selected fromdeuterium, substituted or unsubstituted aryl, and substituted orunsubstituted heteroaryl. Each instance of aryl and heteroaryl can besubstituted with one or more substituents independently selected fromdeuterium, substituted or unsubstituted alkyl, substituted orunsubstituted aryl, and substituted or unsubstituted heteroaryl. Two ormore of these substituents taken together can form a ring system. Insome embodiments, the ring system here is substituted or unsubstitutedaromatic ring, or substituted or unsubstituted aliphatic ring.

In some embodiments, L¹¹ is selected from single bond, substituted orunsubstituted arylene, and substituted or unsubstituted heteroarylene.In some embodiments, each instance of arylene and heteroarylene issubstituted with one or more substituents independently selected fromdeuterium, substituted or unsubstituted alkyl, substituted orunsubstituted aryl, and substituted or unsubstituted heteroaryl; and twoor more of these substituents taken together can form a ring system. Insome embodiments, the ring system here is substituted or unsubstitutedaromatic ring, or substituted or unsubstituted aliphatic ring. In someembodiments, L¹¹ is single bond, unsubstituted phenylene, or phenylenesubstituted with at least one alkyl.

In some embodiments, AA is selected from the group consisting of A1 toA11 shown below. Ph in A11 is unsubstituted phenyl.

In Formula (I), one of D¹, D², D³ and D⁴ is DD; and the others of D¹,D², D³ and D⁴ are selected from H, DD, substituted or unsubstitutedalkyl, substituted or unsubstituted aryl other than Formula (II). Insome embodiments, only one of D¹, D², D³ and D⁴ is DD. In someembodiments, D¹ is DD. In some embodiments, D² is DD. In someembodiments, D³ is DD. In some embodiments, D⁴ is DD. In someembodiments, two of D¹, D², D³ and D⁴ are independently DD. In someembodiments, D¹ and D² are independently DD. In some embodiments, D¹ andD³ are independently DD. In some embodiments, D¹ and D⁴ areindependently DD. In some embodiments, D² and D³ are independently DD.In some embodiments, D² and D⁴ are independently DD. In someembodiments, D³ and D⁴ are independently DD. In some embodiments, threeof D¹, D², D³ and D⁴ are independently DD. In some embodiments, D¹, D²and D³ are independently DD. In some embodiments, D¹, D² and D⁴ areindependently DD. In some embodiments, D¹, D³ and D⁴ are independentlyDD. In some embodiments, D², D³ and D⁴ are independently DD. In someembodiments, D¹, D², D³ and D⁴ are independently DD. When two or moreinstances of DD exist, they may be the same or different. In someembodiments, they are the same.

In some embodiments, only one of D¹, D², D³ and D⁴ is H. In someembodiments, two of D¹, D², D³ and D⁴ are independently H. In someembodiments, three of D¹, D², D³ and D⁴ are independently H. In someembodiments, only one of D¹, D², D³ and D⁴ is substituted orunsubstituted alkyl. In some embodiments, two of D¹, D², D³ and D⁴ areindependently substituted or unsubstituted alkyl. In some embodiments,three of D¹, D², D³ and D⁴ are independently substituted orunsubstituted alkyl. When two or more instances of alkyl exist, they maybe the same or different, in some embodiments, they are the same. Insome embodiments, only one of D¹, D², D³ and D⁴ is substituted orunsubstituted aryl other than Formula (II). In some embodiments, two ofD¹, D², D³ and D⁴ are independently substituted or unsubstituted arylother than Formula (II). In some embodiments, three of D¹, D², D³ and D⁴are independently substituted or unsubstituted aryl other than Formula(II). When two or more instances of aryl exist, they may be the same ordifferent. In some embodiments, they are the same.

DD is represented by Formula (II):

In Formula (II), R¹, R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are independentlyselected from hydrogen, deuterium, substituted or unsubstituted alkyl,substituted or unsubstituted alkoxy, substituted or unsubstituted amino,substituted or unsubstituted aryl, substituted or unsubstituted aryloxy,substituted or unsubstituted heteroaryl, substituted or unsubstitutedheteroaryloxy, and silyl; or two or more of R¹, R², R³, R⁴, R⁵, R⁶, R⁷and R⁸ taken together can form a ring system, or R⁵ and R⁶ takentogether can form single bond.

In some embodiments, the ring system formed by two or more of R¹, R²,R³, R⁴, R⁵, R⁶, R⁷ and R⁸ is substituted or unsubstituted aromatic ring.In some embodiments, the ring system is substituted or unsubstitutedbenzene ring, substituted or unsubstituted naphthalene ring, orsubstituted or unsubstituted anthracene ring. In some embodiments, thearomatic ring is substituted with one or more substituents independentlyselected from hydrogen, deuterium, substituted or unsubstituted alkyl,substituted or unsubstituted alkoxy, substituted or unsubstituted amino,substituted or unsubstituted aryl, substituted or unsubstituted aryloxy,substituted or unsubstituted heteroaryl, substituted or unsubstitutedheteroaryloxy, and silyl.

In Formula (II), L¹ is selected from single bond, substituted orunsubstituted arylene, and substituted or unsubstituted heteroarylene.In some embodiments, each instance of arylene and heteroarylene issubstituted with one or more substituents independently selected fromdeuterium, substituted or unsubstituted alkyl, substituted orunsubstituted aryl, and substituted or unsubstituted heteroaryl; and twoor more of these substituents taken together can form a ring system. Insome embodiments, the ring system here is substituted or unsubstitutedaromatic ring, or substituted or unsubstituted aliphatic ring. In someembodiments, L¹ is single bond, unsubstituted phenylene, or phenylenesubstituted with at least one alkyl.

In some embodiments, DD is

In some embodiments, DD is

In some embodiments, D is

In some embodiments, DD is

In some embodiments, X^(D) is O. In some embodiments, X^(D) is S. Insome embodiments, X^(D) is NR^(D)′. In some embodiments, X^(D) is C(O).In some embodiments, X^(D) is substituted or unsubstituted methylene. Insome embodiments, X^(D) is substituted or unsubstituted ethylene. Insome embodiments, X^(D) is substituted or unsubstituted vinylene. Insome embodiments, X^(D) is substituted or unsubstituted o-arylene. Insome embodiments, X^(D) is and substituted or unsubstitutedo-heteroarylene. In some embodiments, methylene, ethylene, vinylene,o-arylene and o-heteroarylene can be substituted with deuterium,substituted or unsubstituted alkyl, substituted or unsubstituted aryl,and substituted or unsubstituted heteroaryl. In some embodiments, two ormore instances of X^(D) taken together can form a ring system.

In some embodiments, R^(D) is hydrogen. In some embodiments, R^(D) isdeuterium. In some embodiments, R^(D) is substituted or unsubstitutedalkyl. In some embodiments, R^(D) is substituted or unsubstitutedalkoxy. In some embodiments, R^(D) is substituted or unsubstitutedamino. In some embodiments, R^(D) is substituted or unsubstituted aryl.In some embodiments, R^(D) is substituted or unsubstituted aryloxy. Insome embodiments, R^(D) is substituted or unsubstituted heteroaryl. Insome embodiments, R^(D) is substituted or unsubstituted heteroaryloxy.In some embodiments, R^(D) is silyl. In some embodiments, two or moreinstances of R^(D) taken together can form a ring system.

In some embodiments, R^(D)′ is hydrogen. In some embodiments, R^(D)′ isdeuterium. In some embodiments, R^(D)′ is substituted or unsubstitutedalkyl. In some embodiments, R^(D) is substituted or unsubstituted amino.In some embodiments, R^(D)′ is substituted or unsubstituted aryl. Insome embodiments, R^(D)′ is substituted or unsubstituted heteroaryl. Insome embodiments, two or more instances of R^(D)′ and R^(D) takentogether can form a ring system.

In some embodiments, L^(A) is a single bond. In some embodiments, L^(A)is substituted or unsubstituted arylene. In some embodiments, L^(A) issubstituted or unsubstituted heteroarylene.

In some embodiments, L^(D) is a single bond. In some embodiments, L^(D)is substituted or unsubstituted arylene. In some embodiments, L^(D) issubstituted or unsubstituted heteroarylene.

In some embodiments, when L^(A) or L^(D) is substituted each substituentis independently selected from deuterium, substituted or unsubstitutedalkyl, substituted or unsubstituted aryl, and substituted orunsubstituted heteroaryl; two or more of these substituents takentogether can form a ring system.

In some embodiments, DD is selected from the group consisting of D1 toD93 shown below wherein Ph is unsubstituted phenyl,

In some embodiments, A¹ is AA, and D¹, D², D³ and D⁴ are independentlyDD. In some embodiments, A² is AA, and D¹, D², D³ and D⁴ areindependently DD. In some embodiments, A¹ and A² are independently AA,and D¹, D², D³ and D⁴ are independently DD. In some embodiments, A¹ isAA, D¹ is DD, and D², D³ and D⁴ may be independently DD. In someembodiments, A² is AA, D¹ is DD, and D², D³ and D⁴ may be independentlyDD. In some embodiments, A¹ and A² are independently AA, D¹ is DD, andD², D³ and D⁴ may be independently DD. In some embodiments, A¹ is AA, D²is DD, and D¹, D³ and D⁴ may be independently DD. In some embodiments,A² is AA, D² is DD, and D¹, D³ and D⁴ may be independently DD. In someembodiments, A¹ and A² are independently AA, D² is DD, and D¹, D³ and D⁴may be independently DD. In some embodiments, A¹ is AA, D³ is DD, andD¹, D² and D⁴ may be independently DD. In some embodiments, A² is AA, D³is DD, and D¹, D² and D⁴ may be independently DD. In some embodiments,A¹ and A² are independently AA, D³ is DD, and D¹, D² and D⁴ may beindependently DD. In some embodiments, A¹ is AA, D⁴ is DD, and D¹, D²and D³ may he independently DD. In some embodiments, A² is AA, D⁴ is DD,and D¹, D² and D³ may be independently DD. In some embodiments, A¹ andA² are independently AA, D⁴ is DD, and D¹, D² and D³ may beindependently DD. In some embodiments, A¹ is AA, A² is H, one or more ofD¹, D², D³ and D⁴ are independently DD, the others of D¹, D², D³ and D⁴are H. In some embodiments, A¹ is H, A² is AA, one or more of D¹, D², D³and D⁴ are independently DD, the others of D¹, D², D³ and D⁴ are H. Insome embodiments, A¹ and A² are independently AA, one or more of D¹, D²,D³ and D⁴ are independently DD, the others of D¹, D², D³ and D⁴ are H.

In some embodiments, the compound of Formula (I) is selected from

In some embodiments, the compound of Formula (I) is selected from

In some embodiments, the compound of Formula (I) is selected fromCompounds 1 to 506 shown in the following tables:

D¹ D² D³ D⁴ A¹ A² X 1 D21 H H H A1 H O 2 H D21 H H A1 H O 3 H H D21 H A1H O 4 H H H D21 A1 H O 5 D21 H H H H A1 O 6 H D21 H H H A1 O 7 H H D21 HH A1 O 8 H H H D21 H A1 O 9 D21 H H H A1 H S 10 H D21 H H A1 H S 11 H HD21 H A1 H S 12 H H H D21 A1 H S 13 D21 H H H H A1 S 14 H D21 H H H A1 S15 H H D21 H H A1 S 16 H H H D21 H A1 S 17 D21 H H H A1 H N—Ph 18 H D21H H A1 H N—Ph 19 H H D21 H A1 H N—Ph 20 H H H D21 A1 H N—Ph 21 D21 H H HH A1 N—Ph 22 H D21 H H H A1 N—Ph 23 H H D21 H H A1 N—Ph 24 H H H D21 HA1 N—Ph 25 D21 D1 H H A1 H N—Ph 26 D21 D1 D1 H A1 H N—Ph 27 H D1 D21 HA1 A2 N—Ph 28 D1 D1 D1 H A2 H O 29 D1 D1 H D1 A2 H O 30 D1 H D1 D1 A2 HO 31 H D1 D1 D1 A2 H O 32 D1 D1 D1 H H A2 O 33 D1 D1 H D1 H A2 O 34 D1 HD1 D1 H A2 O 35 H D1 D1 D1 H A2 O 36 D1 D1 D1 H A2 H S 37 D1 D1 H D1 A2H S 38 D1 H D1 D1 A2 H S 39 H D1 D1 D1 A2 H S 40 D1 D1 D1 H H A2 S 41 D1D1 H D1 H A2 S 42 D1 H D1 D1 H A2 S 43 H D1 D1 D1 H A2 S 44 D1 D1 D1 HA2 H N—Ph 45 D1 D1 H D1 A2 H N—Ph 46 D1 H D1 D1 A2 H N—Ph 47 H D1 D1 D1A2 H N—Ph 48 D1 D1 D1 H H A2 N—Ph 49 D1 D1 H D1 H A2 N—Ph 50 D1 H D1 D1H A2 N—Ph 51 H D1 D1 D1 H A2 N—Ph 52 D22 D22 H H A1 H O 53 D22 H D22 HA1 H O 54 D22 H H D22 A1 H O 55 H D22 D22 H A1 H O 56 H D22 H D22 A1 H O57 H H D22 D22 A1 H O 58 D22 D22 H H H A1 O 59 D22 H D22 H H A1 O 60 D22H H D22 H A1 O 61 H D22 D22 H H A1 O 62 H D22 H D22 H A1 O 63 H H D22D22 H A1 O 64 D22 D22 H H A1 H S 65 D22 H D22 H A1 H S 66 D22 H H D22 A1H S 67 H D22 D22 H A1 H S 68 H D22 H D22 A1 H S 69 H H D22 D22 A1 H S 70D22 D22 H H H A1 S 71 D22 H D22 H H A1 S 72 D22 H H D22 H A1 S 73 H D22D22 H H A1 S 74 H D22 H D22 H A1 S 75 H H D22 D22 H A1 S 76 D22 D22 H HA1 H N—Ph 77 D22 H D22 H A1 H N—Ph 78 D22 H H D22 A1 H N—Ph 79 H D22 D22H A1 H N—Ph 80 H D22 H D22 A1 H N—Ph 81 H H D22 D22 A1 H N—Ph 82 D22 D22H H H A1 N—Ph 83 D22 H D22 H H A1 N—Ph 84 D22 H H D22 H A1 N—Ph 85 H D22D22 H H A1 N—Ph 86 H D22 H D22 H A1 N—Ph 87 H H D22 D22 H A1 N—Ph 88 D4D4 H H A5 H O 89 D4 H D4 H A5 H O 90 D4 H H D4 A5 H O 91 H D4 D4 H A5 HO 92 H D4 H D4 A5 H O 93 H H D4 D4 A5 H O 94 D4 D4 H H H A5 O 95 D4 H D4H H A5 O 96 D4 H H D4 H A5 O 97 H D4 D4 H H A5 O 98 H D4 H D4 H A5 O 99H H D4 D4 H A5 O 100 D4 D4 H H A5 H S 101 D4 H D4 H A5 H S 102 D4 H H D4A5 H S 103 H D4 D4 H A5 H S 104 H D4 H D4 A5 H S 105 H H D4 D4 A5 H S106 D4 D4 H H H A5 S 107 D4 H D4 H H A5 S 108 D4 H H D4 H A5 S 109 H D4D4 H H A5 S 110 H D4 H D4 H A5 S 111 H H D4 D4 H A5 S 112 D4 D4 H H A5 HN—Ph 113 D4 H D4 H A5 H N—Ph 114 D4 H H D4 A5 H N—Ph 115 H D4 D4 H A5 HN—Ph 116 H D4 H D4 A5 H N—Ph 117 H H D4 D4 A5 H N—Ph 118 D4 D4 H H H A5N—Ph 119 D4 H D4 H H A5 N—Ph 120 D4 H H D4 H A5 N—Ph 121 H D4 D4 H H A5N—Ph 122 H D4 H D4 H A5 N—Ph 123 H H D4 D4 H A5 N—Ph 124 D3 D3 H H A3 HO 125 D3 H D3 H A3 H O 126 D3 H H D3 A3 H O 127 H D3 D3 H A3 H O 128 HD3 H D3 A3 H O 129 H H D3 D3 A3 H O 130 D3 D3 H H H A3 O 131 D3 H D3 H HA3 O 132 D3 H H D3 H A3 O 133 H D3 D3 H H A3 O 134 H D3 H D3 H A3 O 135H H D3 D3 H A3 O 136 D3 D3 H H A3 H S 137 D3 H D3 H A3 H S 138 D3 H H D3A3 H S 139 H D3 D3 H A3 H S 140 H D3 H D3 A3 H S 141 H H D3 D3 A3 H S142 D3 D3 H H H A3 S 143 D3 H D3 H H A3 S 144 D3 H H D3 H A3 S 145 H D3D3 H H A3 S 146 H D3 H D3 H A3 S 147 H H D3 D3 H A3 S 148 D3 D3 H H A3 HN—Ph 149 D3 H D3 H A3 H N—Ph 150 D3 H H D3 A3 H N—Ph 151 H D3 D3 H A3 HN—Ph 152 H D3 H D3 A3 H N—Ph 153 H H D3 D3 A3 H N—Ph 154 D3 D3 H H H A3N—Ph 155 D3 H D3 H H A3 N—Ph 156 D3 H H D3 H A3 N—Ph 157 H D3 D3 H H A3N—Ph 158 H D3 H D3 H A3 N—Ph 159 H H D3 D3 H A3 N—Ph 160 D3 D3 H H A3 A3O 161 D3 H D3 H A3 A3 O 162 D3 H H D3 A3 A3 O 163 H D3 D3 H A3 A3 O 164H D3 H D3 A3 A3 O 165 H H D3 D3 A3 A3 O 166 D3 D3 H H A3 A3 S 167 D3 HD3 H A3 A3 S 168 D3 H H D3 A3 A3 S 169 H D3 D3 H A3 A3 S 170 H D3 H D3A3 A3 S 171 H H D3 D3 A3 A3 S 172 D3 D3 H H A3 A3 N—Ph 173 D3 H D3 H A3A3 N—Ph 174 D3 H H D3 A3 A3 N—Ph 175 H D3 D3 H A3 A3 N—Ph 176 H D3 H D3A3 A3 N—Ph 177 H H D3 D3 A3 A3 N—Ph 178 D86 D86 H H A3 H O 179 D86 H D86H A3 H O 180 D86 H H D86 A3 H O 181 H D86 D86 H A3 H O 182 H D86 H D86A3 H O 183 H H D86 D86 A3 H O 184 D86 D86 H H H A3 O 185 D86 H D86 H HA3 O 186 D86 H H D86 H A3 O 187 H D86 D86 H H A3 O 188 H D86 H D86 H A3O 189 H H D86 D86 H A3 O 190 D86 D86 H H A3 H S 191 D86 H D86 H A3 H S192 D86 H H D86 A3 H S 193 H D86 D86 H A3 H S 194 H D86 H D86 A3 H S 195H H D86 D86 A3 H S 196 D86 D86 H H H A3 S 197 D86 H D86 H H A3 S 198 D86H H D86 H A3 S 199 H D86 D86 H H A3 S 200 H D86 H D86 H A3 S 201 H H D86D86 H A3 S 202 D86 D86 H H A3 H N—Ph 203 D86 H D86 H A3 H N—Ph 204 D86 HH D86 A3 H N—Ph 205 H D86 D86 H A3 H N—Ph 206 H D86 H D86 A3 H N—Ph 207H H D86 D86 A3 H N—Ph 208 D86 D86 H H H A3 N—Ph 209 D86 H D86 H H A3N—Ph 210 D86 H H D86 H A3 N—Ph 211 H D86 D86 H H A3 N—Ph 212 H D86 H D86H A3 N—Ph 213 H H D86 D86 H A3 N—Ph 214 D91 H H H A1 H O 215 H D91 H HA1 H O 216 H H D91 H A1 H O 217 H H H D91 A1 H O 218 D91 H H H H A1 O219 H D91 H H H A1 O 220 H H D91 H H A1 O 221 H H H D91 H A1 O 222 D91 HH H A1 H S 223 H D91 H H A1 H S 224 H H D91 H A1 H S 225 H H H D91 A1 HS 226 D91 H H H H A1 S 227 H D91 H H H A1 S 228 H H D91 H H A1 S 229 H HH D91 H A1 S 230 D91 H H H A1 H N—Ph 231 H D91 H H A1 H N—Ph 232 H H D91H A1 H N—Ph 233 H H H D91 A1 H N—Ph 234 D91 H H H H A1 N—Ph 235 H D91 HH H A1 N—Ph 236 H H D91 H H A1 N—Ph 237 H H H D91 H A1 N—Ph 238 D93 D93H H A4 H O 239 D93 H D93 H A4 H O 240 D93 H H D93 A4 H O 241 H D93 D93 HA4 H O 242 H D93 H D93 A4 H O 243 H H D93 D93 A4 H O 244 D93 D93 H H HA4 O 245 D93 H D93 H H A4 O 246 D93 H H D93 H A4 O 247 H D93 D93 H H A4O 248 H D93 H D93 H A4 O 249 H H D93 D93 H A4 O 250 D93 D93 H H A4 H S251 D93 H D93 H A4 H S 252 D93 H H D93 A4 H S 253 H D93 D93 H A4 H S 254H D93 H D93 A4 H S 255 H H D93 D93 A4 H S 256 D93 D93 H H H A4 S 257 D93H D93 H H A4 S 258 D93 H H D93 H A4 S 259 H D93 D93 H H A4 S 260 H D93 HD93 H A4 S 261 H H D93 D93 H A4 S 262 D93 D93 H H A4 H N—Ph 263 D93 HD93 H A4 H N—Ph 264 D93 H H D93 A4 H N—Ph 265 H D93 D93 H A4 H N—Ph 266H D93 H D93 A4 H N—Ph 267 H H D93 D93 A4 H N—Ph 268 D93 D93 H H H A4N—Ph 269 D93 H D93 H H A4 N—Ph 270 D93 H H D93 H A4 N—Ph 271 H D93 D93 HH A4 N—Ph 272 H D93 H D93 H A4 N—Ph 273 H H D93 D93 H A4 N—Ph 274 D42D42 D42 H A2 H O 275 D42 D42 H D1 A2 H O 276 D42 H D42 D42 A2 H O 277 HD42 D42 D42 A2 H O 278 D42 D42 D42 H H A2 O 279 D42 D42 H D1 H A2 O 280D42 H D42 D42 H A2 O 281 H D42 D42 D42 H A2 O 282 D42 D42 D42 H A2 H S283 D42 D42 H D1 A2 H S 284 D42 H D42 D42 A2 H S 285 H D42 D42 D42 A2 HS 286 D42 D42 D42 H H A2 S 287 D42 D42 H D1 H A2 S 288 D42 H D42 D42 HA2 S 289 H D42 D42 D42 H A2 S 290 D42 D42 D42 H A2 H N—Ph 291 D42 D42 HD1 A2 H N—Ph 292 D42 H D42 D42 A2 H N—Ph 293 H D42 D42 D42 A2 H N—Ph 294D42 D42 D42 H H A2 N—Ph 295 D42 D42 H D1 H A2 N—Ph 296 D42 H D42 D42 HA2 N—Ph 297 H D42 D42 D42 H A2 N—Ph 298 D89 D89 H H A2 H O 299 D89 H D89H A2 H O 300 D89 H H D89 A2 H O 301 H D89 D89 H A2 H O 302 H D89 H D89A2 H O 303 H H D89 D89 A2 H O 304 D89 D89 H H H A2 O 305 D89 H D89 H HA2 O 306 D89 H H D89 H A2 O 307 H D89 D89 H H A2 O 308 H D89 H D89 H A2O 309 H H D89 D89 H A2 O 310 D89 D89 H H A2 H S 311 D89 H D89 H A2 H S312 D89 H H D89 A2 H S 313 H D89 D89 H A2 H S 314 H D89 H D89 A2 H S 315H H D89 D89 A2 H S 316 D89 D89 H H H A2 S 317 D89 H D89 H H A2 S 318 D89H H D89 H A2 S 319 H D89 D89 H H A2 S 320 H D89 H D89 H A2 S 321 H H D89D89 H A2 S 322 D89 D89 H H A2 H N—Ph 323 D89 H D89 H A2 H N—Ph 324 D89 HH D89 A2 H N—Ph 325 H D89 D89 H A2 H N—Ph 326 H D89 H D89 A2 H N—Ph 327H H D89 D89 A2 H N—Ph 328 D89 D89 H H H A2 N—Ph 329 D89 H D89 H H A2N—Ph 330 D89 H H D89 H A2 N—Ph 331 H D89 D89 H H A2 N—Ph 332 H D89 H D89H A2 N—Ph 333 H H D89 D89 H A2 N—Ph 334 D87 D87 D87 H A2 H O 335 D87 D87H D87 A2 H O 336 D87 H D87 D87 A2 H O 337 H D87 D87 D87 A2 H O 338 D87D87 D87 D87 A2 H O 339 D87 D87 D87 H H A2 O 340 D87 D87 H D87 H A2 O 341D87 H D87 D87 H A2 O 342 H D87 D87 D87 H A2 O 343 D87 D87 D87 D87 H A2 O344 D87 D87 D87 H A2 H S 345 D87 D87 H D87 A2 H S 346 D87 H D87 D87 A2 HS 347 H D87 D87 D87 A2 H S 348 D87 D87 D87 D87 A2 H S 349 D87 D87 D87 HH A2 S 350 D87 D87 H D87 H A2 S 351 D87 H D87 D87 H A2 S 352 H D87 D87D87 H A2 S 353 D87 D87 D87 D87 H A2 S 354 D87 D87 D87 H A2 H N—Ph 355D87 D87 H D87 A2 H N—Ph 356 D87 H D87 D87 A2 H N—Ph 357 H D87 D87 D87 A2H N—Ph 358 D87 D87 D87 D87 A2 H N—Ph 359 D87 D87 D87 H H A2 N—Ph 360 D87D87 H D87 H A2 N—Ph 361 D87 H D87 D87 H A2 N—Ph 362 H D87 D87 D87 H A2N—Ph 363 D87 D87 D87 D87 H A2 N—Ph 364 D87 D87 D87 H A2 A2 O 365 D87 D87H D87 A2 A2 O 366 D87 H D87 D87 A2 A2 O 367 H D87 D87 D87 A2 A2 O 368D87 D87 D87 D87 A2 A2 O 369 D87 D87 D87 H A2 A2 S 370 D87 D87 H D87 A2A2 S 371 D87 H D87 D87 A2 A2 S 372 H D87 D87 D87 A2 A2 S 373 D87 D87 D87D87 A2 A2 S 374 D87 D87 D87 H A2 A2 N—Ph 375 D87 D87 H D87 A2 A2 N—Ph376 D87 H D87 D87 A2 A2 N—Ph 377 H D87 D87 D87 A2 A2 N—Ph 378 D87 D87D87 D87 A2 A2 N—Ph 379 D86 D86 D86 H A3 H O 380 D86 D86 H D86 A3 H O 381D86 H D86 D86 A3 H O 382 H D86 D86 D86 A3 H O 383 D86 D86 D86 H H A3 O384 D86 D86 H D86 H A3 O 385 D86 H D86 D86 H A3 O 386 H D86 D86 D86 H A3O 387 D86 D86 D86 H A3 H S 388 D86 D86 H D86 A3 H S 389 D86 H D86 D86 A3H S 390 H D86 D86 D86 A3 H S 391 D86 D86 D86 H H A3 S 392 D86 D86 H D86H A3 S 393 D86 H D86 D86 H A3 S 394 H D86 D86 D86 H A3 S 395 D86 D86 D86H A3 H N—Ph 396 D86 D86 H D86 A3 H N—Ph 397 D86 H D86 D86 A3 H N—Ph 398H D86 D86 D86 A3 H N—Ph 399 D86 D86 D86 H H A3 N—Ph 400 D86 D86 H D86 HA3 N—Ph 401 D86 H D86 D86 H A3 N—Ph 402 H D86 D86 D86 H A3 N—Ph 403 D92H H H A2 H O 404 H D92 H H A2 H O 405 H H D92 H A2 H O 406 H H H D92 A2H O 407 D92 H H H H A2 O 408 H D92 H H H A2 O 409 H H D92 H H A2 O 410 HH H D92 H A2 O 411 D92 H H H A2 H S 412 H D92 H H A2 H S 413 H H D92 HA2 H S 414 H H H D92 A2 H S 415 D92 H H H H A2 S 416 H D92 H H H A2 S417 H H D92 H H A2 S 418 H H H D92 H A2 S 419 D92 H H H A2 H N—Ph 420 HD92 H H A2 H N—Ph 421 H H D92 H A2 H N—Ph 422 H H H D92 A2 H N—Ph 423D92 H H H H A2 N—Ph 424 H D92 H H H A2 N—Ph 425 H H D92 H H A2 N—Ph 426H H H D92 H A2 N—Ph 427 H H D2 H A2 A2 N—Ph 428 H H D5 H A2 A2 N—Ph 429H H D6 H A2 A2 N—Ph 430 H H D7 H A2 A2 N—Ph 431 H H D8 H A2 A2 N—Ph 432H H D9 H A2 A2 N—Ph 433 H H D10 H A2 A2 N—Ph 434 H H D11 H A2 A2 N—Ph435 H H D12 H A2 A2 N—Ph 436 H H D13 H A2 A2 N—Ph 437 H H D14 H A2 A2N—Ph 438 H H D15 H A2 A2 N—Ph 439 H H D16 H A2 A2 N—Ph 440 H H D17 H A2A2 N—Ph 441 H H D18 H A2 A2 N—Ph 442 H H D19 H A2 A2 N—Ph 443 H H D20 HA2 A2 N—Ph 444 H H D23 H A2 A2 N—Ph 445 H H D24 H A2 A2 N—Ph 446 H H D25H A2 A2 N—Ph 447 H H D26 H A2 A2 N—Ph 448 H H D27 H A2 A2 N—Ph 449 H HD28 H A2 A2 N—Ph 450 H H D29 H A2 A2 N—Ph 451 H H D30 H A2 A2 N—Ph 452 HH D31 H A2 A2 N—Ph 453 H H D32 H A2 A2 N—Ph 454 H H D33 H A2 A2 N—Ph 455H H D34 H A2 A2 N—Ph 456 H H D35 H A2 A2 N—Ph 457 H H D36 H A2 A2 N—Ph458 H H D37 H A2 A2 N—Ph 459 H H D38 H A2 A2 N—Ph 460 H H D39 H A2 A2N—Ph 461 H H D40 H A2 A2 N—Ph 462 H H D41 H A2 A2 N—Ph 463 H H D43 H A2A2 N—Ph 464 H H D44 H A2 A2 N—Ph 465 H H D45 H A2 A2 N—Ph 466 H H D46 HA2 A2 N—Ph 467 H H D47 H A2 A2 N—Ph 468 H H D48 H A2 A2 N—Ph 469 H H D49H A2 A2 N—Ph 470 H H D50 H A2 A2 N—Ph 471 H H D51 H A2 A2 N—Ph 472 H HD52 H A2 A2 N—Ph 473 H H D53 H A2 A2 N—Ph 474 H H D54 H A2 A2 N—Ph 475 HH D55 H A2 A2 N—Ph 476 H H D56 H A2 A2 N—Ph 477 H H D57 H A2 A2 N—Ph 478H H D58 H A2 A2 N—Ph 479 H H D59 H A2 A2 N—Ph 480 H H D60 H A2 A2 N—Ph481 H H D61 H A2 A2 N—Ph 482 H H D62 H A2 A2 N—Ph 483 H H D63 H A2 A2N—Ph 484 H H D64 H A2 A2 N—Ph 485 H H D65 H A2 A2 N—Ph 486 H H D66 H A2A2 N—Ph 487 H H D67 H A2 A2 N—Ph 488 H H D68 H A2 A2 N—Ph 489 H H D69 HA2 A2 N—Ph 490 H H D70 H A2 A2 N—Ph 491 H H D71 H A2 A2 N—Ph 492 H H D72H A2 A2 N—Ph 493 H H D73 H A2 A2 N—Ph 494 H H D74 H A2 A2 N—Ph 495 H HD75 H A2 A2 N—Ph 496 H H D76 H A2 A2 N—Ph 497 H H D77 H A2 A2 N—Ph 498 HH D78 H A2 A2 N—Ph 499 H H D79 H A2 A2 N—Ph 500 H H D80 H A2 A2 N—Ph 501H H D81 H A2 A2 N—Ph 502 H H D82 H A2 A2 N—Ph 503 H H D83 H A2 A2 N—Ph504 H H D84 H A2 A2 N—Ph 505 H H D85 H A2 A2 N—Ph 506 H H D90 H A2 A2N—Ph

In some embodiments, compounds of Formula (I) are substituted at leastone deuterium.

In some embodiments, compounds of Formula (I) are light-emittingmaterials.

In some embodiments, compounds of Formula (I) are compound capable ofemitting delayed fluorescence.

In some embodiments, compounds of Formula (I) are light-emittingmaterials.

In some embodiments of the present disclosure, when excited via thermalor electronic means, the compounds of Formula (I) can produce light inUV region, the blue, green, yellow, orange, or red region of the visiblespectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600nm, or about 600 nm to about 700 nm), or near-IR region.

In some embodiments of the present disclosure, when excited via thermalor electronic means, the compounds of Formula (I) can produce light inthe red or orange region of the visible spectrum (e.g., about 620 nm toabout 780 nm; about 650 nm).

In some embodiments of the present disclosure, when excited via thermalor electronic means, the compounds of Formula (I) can produce light inthe orange or yellow region of the visible spectrum (e.g., about 570 nmto about 620 nm; about 590 nm; about 570 nm).

In some embodiments of the present disclosure, when excited via thermalor electronic means, the compounds of Formula (I) can produce light inthe green region of the visible spectrum (e.g., about 490 nm to about575 nm; about 510 nm).

In some embodiments of the present disclosure, when excited via thermalor electronic means, the compounds of Formula (I) can produce light inthe blue region of the visible spectrum (e.g., about 400 nm to about 490nm; about 475 nm).

Electronic properties of a library of small chemical molecules can becomputed. using known ab initio quantum mechanical computations. Forexample, using a time-dependent density functional theory using, as abasis set, the set of functions known as 6-31G* and a Becke,3-parameter, Lee-Yang-Parr hybrid functional to solve Hartree-Fockequations (TD-DFT/B3LYP/6-31G*), molecular fragments (moieties) can bescreened which have HOMOs above a specific threshold and LUMOs below aspecific threshold, and wherein the calculated triplet state of themoieties is above 2.75 eV.

Therefore, for example, a donor moiety can be selected because it has aHOMO energy (e.g., an ionization potential) of greater than or equal to−6.5 eV. An acceptor moiety (“A”) can be selected because it has, forexample, a LUMO energy (e.g., an electron affinity) of less than orequal to −0.5 eV. The bridge moiety (“B”) can be a rigid conjugatedsystem that can, for example, sterically restrict the acceptor and donormoieties into a specific configuration, thereby preventing the overlapbetween the conjugated π system of donor and acceptor moieties.

In some embodiments, the compound library is filtered using one or moreof the following properties:

-   1. emission near a certain wavelength;-   2. calculated triplet state above a certain energy level;-   3. ΔE_(ST) value below a certain value;-   4. quantum yield above a certain value;-   5. HOMO level; and-   6. LUMO level.

In some embodiments, the difference between the lowest singlet excitedstate and the lowest triplet excited state at 77K (ΔE_(ST)) is less thanabout (15 eV, less than about 0.4 eV, less than about 0.3 eV, less thanabout 0.2 eV, or less than about 0.1 eV. In some embodiments, theΔE_(ST) value is less than about 0.09 eV, less than about 0.08 eV, lessthan about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV,less than about 0.04 eV, less than about 0.03 eV, less than about 0.02eV, or less than about 0.01 eV.

In some embodiments, a compound of Formula (I) exhibits a quantum yieldof greater than 25%, such as about 30%, about 35%, about 40%, about 45%,about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about80%, about 85%, about 90%, about 95%, or greater.

Compositions with the Disclosed Compounds

In some embodiments, a compound of Formula (I) is combined with,dispersed within, covalently bonded to, coated with, formed on, orotherwise associated with, one or more materials (e.g., small molecules,polymers, metals, metal complexes, etc.) to form a film or layer insolid state. For example, the compound of Formula (I) may be combinedwith an electroactive material to form a film. In some cases, thecompound of Formula (I) may be combined with a hole-transport polymer.In some cases, the compound of Formula (I) may be combined with anelectron-transport polymer. In some cases, the compound of Formula (I)may be combined with a hole-transport polymer and an electron-transportpolymer. In some cases, the compound of Formula (I) may be combined witha copolymer comprising both hole-transport portions andelectron-transport portions. In such embodiments, electrons and/or holesformed within the solid film or layer may interact with the compound ofFormula (I).

Film Formation

In some embodiments, a film containing a compound of the presentinvention of Formula (I) can be formed in a wet process. In a wetprocess, a solution prepared by dissolving a composition containing acompound of the present invention is applied to a surface and formedinto a film thereon after solvent removal. A wet process includes,though not limited thereto, a spin coating method, a slit coatingmethod, a spraying method, an inkjet method (a spay method), a gravureprinting method, an offset printing method, and a flexographic printingmethod. In a wet process, a suitable organic solvent capable ofdissolving a composition containing a compound of the present inventionis selected and used. In some embodiments, a substituent (for example,an alkyl group) capable of increasing solubility in an organic solventcan be introduced into the compound contained in the composition.

In some embodiments, a film containing a compound of the presentinvention can be formed in a dry process. In some embodiments, a dryprocess includes a vacuum evaporation method, but is not limitedthereto. In the case of employing a vacuum evaporation method, compoundsto constitute a film can be vapor-co-deposited from individualevaporation sources, or can be vapor-co-deposited from a singleevaporation source of a mixture of the compounds. In the case of using asingle evaporation source, a mixed powder prepared by mixing powders ofcompounds may be used, or a compression-molded body prepared bycompressing the mixed powder may be used, or a mixture prepared byheating, melting and cooling compounds may be used. In some embodimentswhere vapor-co-deposition is carried out under such a condition that theevaporation rate (weight reduction rate) of the plural compoundscontained in a single evaporation source is the same or is nearly thesame as each other, a film whose composition ratio corresponds to thecomposition ratio of the plural compounds contained in the evaporationsource can be formed. Under the condition where plural compounds aremixed to make an evaporation source in a composition ratio that is thesame as the composition ratio of the film to be formed, a film having adesired composition ratio can be formed in a simplified manner. In someembodiments where a temperature at which the compounds to bevapor-co-deposited could have the same weight reduction ratio isidentified, and the temperature can be employed as the temperature invapor-co-deposition.

Exemplary Uses of the Disclosed Compounds Organic Light-Emitting Diodes

One aspect of the invention relates to use of the compound of Formula(I) of the invention as a light-emitting material of an organiclight-emitting device. In some embodiments, the compound represented byFormula (I) of the invention may be effectively used as a light-emittingmaterial in a light-emitting layer of an organic light-emitting device.In some embodiments, the compound of Formula (I) comprises a delayedfluorescent material emitting delayed fluorescent light (delayedfluorescence emitter). In some embodiments, the invention provides adelayed fluorescence emitter having the structure of Formula (I). Insome embodiments, the invention relates to the use of the compound ofFormula (I) as the delayed fluorescence emitter. In some embodiments,the compound of Formula (I) can be used as a host material and used withone or more light-emitting materials, and the light-emitting materialcan be a fluorescent material, a phosphorescent material or a TADFmaterial. In some embodiments, the compound of Formula (I) can be usedas an assistant dopant and used with one or more light-emittingmaterials and one or more host materials, and the light-emittingmaterial can be a fluorescent material, a phosphorescent material or aTADF material. In some embodiments, the compound of Formula (I) can beused as a hole transport material. In some embodiments, the compound ofFormula (I) can be used as an electron transport material. In someembodiments, the invention relates to a method for emitting delayedfluorescent light from the compound of Formula (I). In some embodiments,an organic light-emitting device comprising the compound as alight-emitting material, emits delayed fluorescent light, and has a highlight emission efficiency.

In some embodiments, a light-emitting layer comprises a compound ofFormula (I), wherein the compound of Formula (I) is oriented parallel tothe substrate. In some embodiments, the substrate is a film formingsurface. In some embodiments, the orientation of the compound of Formula(I) with respect to the film forming surface influences or determinesthe propagation directions of the light emitted by the compound to bealigned. In some embodiments, the alignment of the propagationdirections of the light emitted by the compound of Formula (I) enhancesthe light extraction efficiency from the light-emitting layer.

One aspect of the invention relates to an organic light-emitting device.In some embodiments, the organic light-emitting device comprises alight-emitting layer. In some embodiments, the light-emitting layercomprises a compound of Formula (I) as a light-emitting material, Insome embodiments, the organic light-emitting device is an organicphotoluminescent device (organic PL device). In some embodiments, theorganic light-emitting device is an organic electroluminescent device(organic EL device). In some embodiments, the compound of Formula (I)assists the light emission of another light-emitting material comprisedin the light-emitting layer, i.e., as a so-called assistant dopant. Insome embodiments, the compound of Formula (I) comprised in thelight-emitting layer is in its the lowest excited singlet energy level,which is comprised between the lowest excited singlet energy level ofthe host material comprised in the light-emitting layer and the lowestexcited singlet energy level of the another light-emitting materialcomprised in the light-emitting layer.

In some embodiments, the organic photoluminescent device comprises atleast one light-emitting layer. In some embodiments, the organicelectroluminescent device comprises at least an anode, a cathode, and anorganic layer between the anode and the cathode. In some embodiments,the organic layer comprises at least a light-emitting layer. In someembodiments, the organic layer comprises only a light-emitting layer. Insome embodiments, the organic layer, comprises one or more organiclayers in addition to the light-emitting layer. Examples of the organiclayer include a hole transporting layer, a hole injection layer, anelectron barrier layer, a hole barrier layer, an electron injectionlayer, an electron transporting layer and an exciton barrier layer. Insome embodiments, the hole transporting layer may be a hole injectionand transporting layer having a hole injection function, and theelectron transporting layer may be an electron injection andtransporting layer having an electron injection function. An example ofan organic electroluminescent device is shown in FIG. 1.

Substrate

In some embodiments, the organic electroluminescent device of theinvention is supported by a substrate, wherein the substrate is notparticularly limited and may he any of those that have been commonlyused in an organic electroluminescent device, for example those formedof glass, transparent plastics, quartz and silicon.

Anode

In some embodiments, the anode of the organic electroluminescent deviceis made of a metal, an alloy, an electroconductive compound, or acombination thereof. In some embodiments, the metal, alloy, orelectroconductive compound has a large work function (4 eV or more). Insome embodiments, the metal is Au. In some embodiments, theelectroconductive transparent material is selected from CuI, indium tinoxide (ITO), SnO₂, and ZnO. In some embodiments, an amorphous materialcapable of forming a transparent electroconductive film, such as IDIXO(In₂O₃—ZnO), is be used. In some embodiments, the anode is a thin film.In some embodiments the thin film is made by vapor deposition orsputtering, In some embodiments, the film is patterned by aphotolithography method. In some embodiments, where the pattern may notrequire high accuracy (for example, approximately 100 μm or more), thepattern may be formed with a mask having a desired shape on vapordeposition or sputtering of the electrode material. In some embodiments,when a material can be applied as a coating, such as an organicelectroconductive compound, a wet film forming method, such as aprinting method and a coating method is used. In some embodiments, whenthe emitted light goes through the anode, the anode has a transmittanceof more than 10%, and the anode has a sheet resistance of severalhundred Ohm per square or less. In some embodiments, the thickness ofthe anode is from 10 to 1,000 nm. In some embodiments, the thickness ofthe anode is from 10 to 200 nm. In some embodiments, the thickness ofthe anode varies depending on the material used.

Cathode

In some embodiments, the cathode is made of an electrode material ametal having a small work function (4 eV or less) (referred to as anelectron injection metal), an alloy, an electroconductive compound, or acombination thereof In some embodiments, the electrode material isselected from sodium, a sodium-potassium alloy, magnesium, lithium, amagnesium-supper mixture, a magnesium-silver mixture, amagnesium-aluminum mixture, a magnesium-indium mixture, analuminum-aluminum oxide (Al₂O₃) mixture, indium, a lithium-aluminummixture, and a rare earth metal. In some embodiments, a mixture of anelectron injection metal and a second metal that is a stable metalhaving a larger work function than the electron injection metal is used.In some embodiments, the mixture is selected from a magnesium-silvermixture, a magnesium-aluminum mixture, a magnesium-indium mixture, analuminum-aluminum oxide (Al₂O₃) mixture, a lithium-aluminum mixture, andaluminum. In some embodiments, the mixture increases the electroninjection property and the durability against oxidation. In someembodiments, the cathode is produced by forming the electrode materialinto a thin film by vapor deposition or sputtering. In some embodiments,the cathode has a sheet resistance of several hundred Ohm per square orless. In some embodiments, the thickness of the cathode ranges from 10nm to 5 μm. In some embodiments, the thickness of the cathode rangesfrom 50 to 200 nm. In some embodiments, for transmitting the emittedlight, any one of the anode and the cathode of the organicelectroluminescent device is transparent or translucent. In someembodiments, the transparent or translucent electroluminescent devicesenhances the light emission luminance.

In some embodiments, the cathode is formed with an electroconductivetransparent material, as described for the anode, to form a transparentor translucent cathode. In some embodiments, a device comprises an anodeand a cathode, both being transparent or translucent.

Light-Emitting Layer

In some embodiments, the light-emitting layer is a layer, in which holesand electrons, injected respectively from the anode and the cathode, arerecombined to form excitons. In some embodiments the layer emits light.

In some embodiments, a light-emitting material is solely used as thelight-emitting layer. In some embodiments, the light-emitting layercontains a light-emitting material, and a host material. In someembodiments, the light-emitting material is one or more compounds ofFormula (I). In some embodiments, for the organic electroluminescentdevice and the organic photoluminescent device to exhibit a high lightemission efficiency, the singlet excitons and the triplet excitonsgenerated in the light-emitting material are confined in thelight-emitting material. In some embodiments, a host material is used inaddition to the light-emitting material in the light-emitting layer. Insome embodiments, the host material is an organic compound. In someembodiments, the organic compounds have excited singlet energy andexcited triplet energy, at least one of which is higher than those ofthe light-emitting material of the invention. In some embodiments, thesinglet excitons and the triplet excitons generated in thelight-emitting material of the invention are confined in the moleculesof the light-emitting material of the invention. In some embodiments,the singlet and triplet excitons are sufficiently confined to elicit thelight emission efficiency. In some embodiments, the singlet excitons andthe triplet excitons are not confined sufficiently, though a high lightemission efficiency is still obtained, and thus a host material capableof achieving a high light emission efficiency can be used in theinvention without any particular limitation. In some embodiments, thelight emission occurs in the light-emitting material of thelight-emitting layer in the devices of the invention. In someembodiments, the emitted light contains both fluorescent light anddelayed fluorescent light. In some embodiments, the emitted lightcomprises emitted light from the host material. In some embodiments, theemitted light consists of emitted light from the host material. In someembodiments, the emitted light comprises emitted light from a compoundof Formula (I), and emitted light from the host material. In someembodiments, a TADF molecule and a host material are used. In someembodiments, the TADF will be assistant dopant.

In some embodiments, when a host material is used, the amount of thecompound of the invention as the light-emitting material contained inthe light-emitting layer is 0.1% by weight or more. In some embodiments,when a host material is used, the amount of the compound of theinvention as the light-emitting material contained in the light-emittinglayer is 1% by weight or more. In some embodiments, when a host materialis used, the amount of the compound of the invention as thelight-emitting material contained in the light-emitting layer is 50% byweight or less. In some embodiments, when a host material is used, theamount of the compound of the invention as the light-emitting materialcontained in the light-emitting layer is 20% by weight or less. In someembodiments, when a host material is used, the amount of the compound ofthe invention as the light-emitting material contained in thelight-emitting layer is 10% by weight or less.

In some embodiments, the host material in the light-emitting layer is anorganic compound comprising a hole transporting function and an electrontransporting function. In some embodiments, the host material in thelight-emitting layer is an organic compound that prevents the emittedlight from being increased in wavelength. In some embodiments, the hostmaterial in the light-emitting layer is an organic compound with a highglass transition temperature.

In some embodiments, a light-emitting layer contains two or more typesof TADF molecules differing in the structure. For example, alight-emitting layer may contain three types of materials of a hostmaterial, a first TADF molecule and a second TADF molecule whose excitedsinglet energy level is higher in that order. In that case, preferably,the first TADF molecule and the second TADF molecule are both such thatthe difference between the lowest excited singlet energy level and thelowest excited triplet energy level at 77 K, ΔE_(ST), is 0.3 eV or less,more preferably 0.25 eV or less, even more preferably 0.2 eV or less,still more preferably 0.15 eV or less, still further more preferably 0.1eV or less, still further more preferably 0.07 eV or less, still furthermore preferably 0.05 eV or less, still further more preferably 0.03 eVor less, and especially further more preferably 0.01 eV or less.Preferably, the content of the first TADF molecule in the light-emittinglayer is larger than the content of the second TADF molecule therein.Also preferably, the content of the host material in the light-emittinglayer is larger than the content of the second TADF molecule therein,The content of the first TADF molecule in the light-emitting layer maybe larger than, or may be smaller than, or may be the same as thecontent of the host material therein. In some embodiments, thecomposition in the light-emitting layer may be such that the hostmaterial is 10 to 70% by weight, the first TADF molecule is 10 to 80% byweight, and the second TADF molecule is 0.1 to 30% by weight. In someembodiments, the composition in the light-emitting layer may be suchthat the host material is 20 to 45% by weight, the first TADF moleculeis 50 to 75% by weight, and the second TADF molecule is 5 to 20% byweight, in some embodiments, the luminescence quantum yield byphotoexcitation, ϕPL1(A), of a vapor-co-deposited film of a first TADFmolecule and a host material (the content of the first TADF molecule inthe vapor-co-deposited film=A % by weight), and the luminescence quantumyield by photoexcitation, ϕPL2(A), of a vapor-co-deposited film of asecond TADF molecule and a host material (the content of the second TADFmolecule in the vapor-co-deposited film=A % by weight) satisfy arelational expression ϕPL1(A)>ϕPL2(A). In some embodiments, theluminescence quantum yield by photoexcitation, ϕPL2(B), of avapor-co-deposited film of a second TADF molecule and a host material(the content of the second TADF molecule in the vapor-co-depositedfilm=B % by weight), and the luminescence quantum yield byphotoexcitation, ϕPL2(100), of a neat film of a second TADF moleculesatisfy a relational expression ϕPL2(B)>ϕPL2(100). In some embodiments,the light-emitting layer may contain three types of TADF moleculesdiffering in the structure. The compound of the present invention may beany of plural TADF compounds contained in the light-emitting layer.

In some embodiments, the light-emitting layer may be composed of amaterial selected from the group consisting of a host material, anassistant dopant and a light-emitting material. In some embodiments, thelight-emitting layer does not contain a metal element. In someembodiments, the light-emitting layer may be formed of a materialcomposed of atoms alone selected from the group consisting of a carbonatom, a hydrogen atom, a nitrogen atom, an oxygen atom and a sulfuratom. Alternatively, the light-emitting layer may he formed of amaterial composed of atoms alone selected from the group consisting of acarbon atom, a hydrogen atom and a nitrogen atom.

When the light-emitting layer contains any other TADF material than thecompound of the present invention, the TADF material may be a knowndelayed fluorescent material. Preferred delayed fluorescent materialsinclude compounds included in general formulae described inWO2013/154064, paragraphs 0008 to 0048 and 0095 to 0133; WO2013/011954,paragraphs 0007 to 0047 and 0073 to 0085; WO2013/011955, paragraphs 0007to 0033 and 0059 to 0066; WO2013/081088, paragraphs 0008 to 0071 and0118 to 0133; JP 2013-256490A, paragraphs 0009 to 0046 and 0093 to 0134;JP 2013-116975A, paragraphs 0008 to 0020 and 0038 to 0040;WO2013/133359, paragraphs 0007 to 0032 and 0079 to 0084; WO2013/161437,paragraphs 0008 to 0054 and 0101 to 0121; JP 2014-9352A, paragraphs 0007to 0041 and 0060 to 0069; JP 2014-9224A, paragraph 0008 to 0048 and 0067to 0076; JP 2017-119663A, paragraphs 0013 to 0025; JP 2017-119664A,paragraphs 0013 to 0026; JP 2017-222623A, paragraphs 0012 to 0025; JP2017-226838A, paragraphs 0010 to 0050; JP 2018-100411A, paragraphs 0012to 0043; WO2018/047853, paragraphs 0016 to 0044; and especiallyexemplified compounds therein capable of emitting delayed fluorescence.Also, light-emitting materials described in JP 2013-253121A,WO2013/133359, WO2014/034535, WO2014/115743, WO2014/122895,WO2014/126200, WO2014/136758, WO2014/133121, WO2014/136860,WO2014/196585, WO2014/189122, WO2014/168101, WO2015/008580,WO2014/203840, WO2015/002213, WO2015/016200, WO2015/019725,WO2015/072470, WO2015/108049, WO2015/080182, WO2015/072537,WO2015/080183, JP 2015-129240A, WO2015/129714, WO2015/129715,WO2015/133501, WO2015/136880, WO2015/137244, WO2015/137202,WO2015/137136, WO2015/146541 and WO2015/159541, and capable of emittingdelayed fluorescence may preferably be employed here. The patentpublications described in this paragraph are herein incorporated byreference as a part of the present disclosure.

Injection Layer

An injection layer is a layer between the electrode and the organiclayer. In some embodiments, the injection layer decreases the drivingvoltage and enhances the light emission luminance. In some embodimentsthe injection layer includes a hole injection layer and an electroninjection layer. The injection layer can be positioned between the anodeand the light-emitting layer or the hole transporting layer, and betweenthe cathode and the light-emitting layer or the electron transportinglayer. In some embodiments, an injection layer is present. In someembodiments, no injection layer is present.

Barrier Layer

A barrier layer is a layer capable of inhibiting charges (electrons orholes) and/or excitons present in the light-emitting layer from beingdiffused outside the light-emitting layer. In some embodiments, theelectron barrier layer is between the light-emitting layer and the holetransporting layer and inhibits electrons from passing through thelight-emitting layer toward the hole transporting layer. In someembodiments, the hole barrier layer is between the light-emitting layerand the electron transporting layer and inhibits holes from passingthrough the light-emitting layer toward the electron transporting layer.In some embodiments, the barrier layer inhibits excitons from beingdiffused outside the light-emitting layer. In some embodiments, theelectron barrier layer and the hole barrier layer are exciton barrierlayers. As used herein, the term “electron barrier layer” or “excitonbarrier layer” includes a layer that has the functions of both electronbarrier layer and of an exciton barrier layer.

Hole Barrier Layer

A hole barrier layer acts as an electron transporting layer. In someembodiments, the hole barrier layer inhibits holes from reaching theelectron transporting layer while transporting electrons. In someembodiments, the hole barrier layer enhances the recombinationprobability of electrons and holes in the light-emitting layer. Thematerial for the hole barrier layer may be the same materials as theones described for the electron transporting layer.

Electron Barrier Layer

As electron barrier layer transports holes. In some embodiments, theelectron barrier layer inhibits electrons from reaching the holetransporting layer while transporting holes. In some embodiments, theelectron barrier layer enhances the recombination probability ofelectrons and holes in the light-emitting layer.

Exciton Barrier Layer

An exciton barrier layer inhibits excitons generated throughrecombination of holes and electrons in the light-emitting layer frombeing diffused to the charge transporting layer. In some embodiments,the exciton barrier layer enables effective confinement of excitons inthe light-emitting layer. In some embodiments, the light emissionefficiency of the device is enhanced. In some embodiments, the excitonbarrier layer is adjacent to the light-emitting layer on any of the sideof the anode and the side of the cathode, and on both the sides. In someembodiments, where the exciton barrier layer is on the side of theanode, the layer can be between the hole transporting layer and thelight-emitting layer and adjacent to the light-emitting layer. In someembodiments, where the exciton barrier layer is on the side of thecathode, the layer can be between the light-emitting layer and thecathode and adjacent to the light-emitting layer. In some embodiments, ahole injection layer, an electron barrier layer, or a similar layer isbetween the anode and the exciton barrier layer that is adjacent to thelight-emitting layer on the side of the anode. In some embodiments, ahole injection layer, an electron harrier layer, a hole harrier layer,or a similar layer is between the cathode and the exciton barrier layerthat is adjacent to the light-emitting layer on the side of the cathode.In some embodiments, the exciton barrier layer comprises excited singletenergy and excited triplet energy, at least one of which is higher thanthe excited singlet energy and the excited triplet energy of thelight-emitting material, respectively.

Hole Transporting Layer

The hole transporting layer comprises a hole transporting material. Insome embodiments, the hole transporting layer is a single layer. In someembodiments, the hole transporting layer comprises a. plurality oflayers.

In some embodiments, the hole transporting material has one of injectionor transporting property of holes and barrier property of electrons. Insome embodiments, the hole transporting material is an organic material.In some embodiments, the hole transporting material is an inorganicmaterial. Examples of known hole transporting materials that may be usedherein include but are not limited to a triazole derivative, anoxadiazole derivative, an imidazole derivative, a carbazole derivative,an indolocarbazole derivative, a polyarylalkane derivative, a pyrazolinederivative, a pyrazolone derivative, a phenylenediamine derivative, anarylamine derivative, an amino-substituted chalcone derivative, anoxazole derivative, a styrylanthracene derivative, a fluorenonederivative, a hydrazone derivative, a stilbene derivative, a silazanederivative, an aniline copolymer and electroconductive polymer oligomer,particularly a thiophene oligomer, or a combination thereof. In someembodiments, the hole transporting material is selected from a porphyrincompound, an aromatic tertiary amine compound, and a styrylaminecompound. In some embodiments, the hole transporting material is anaromatic tertiary amine compound.

Electron-Transporting Layer

The electron-transporting layer comprises an electron transportingmaterial. In some embodiments, the electron-transporting layer is asingle layer. In some embodiments, the electron-transporting layercomprises a plurality of layer.

In some embodiments, the electron transporting material needs only tohave a function of transporting electrons, which are injected from thecathode, to the light-emitting layer. In some embodiments, the electrontransporting material also function as a hole barrier material. Examplesof the electron transporting layer that may he used herein include butare not limited to a nitro-substituted fluorene derivative, adiphenylquinone derivative, a thiopyran dioxide derivative,carbodiimide, a fluorenylidene methane derivative, anthraquinodimethane,an anthrone derivatives, an oxadiazole derivative, an azole derivative,an azine derivative, or a combination thereof, or a polymer thereof. Insome embodiments, the electron transporting material is a thiadiazolederivative, or a quinoxaline derivative. In some embodiments, theelectron transporting material is a polymer material.

In some embodiments, a compound of Formula (I) is comprised in thelight-emitting layer of a device of the invention. In some embodiments,a compound of Formula (I) is comprised in the light-emitting layer andat least one other layers. In some embodiments, the compounds of Formula(I) are independently selected for each layer. In some embodiments, thecompounds of Formula (I) are the same. In some embodiments, thecompounds of Formula (I) are different. For example, the compoundrepresented by Formula (I) may be used in the injection layer, thebarrier layer, the hole barrier layer, the electron barrier layer, theexciton barrier layer, the hole transporting layer, the electrontransporting layer and the like described above. The film forming methodof the layers are not particularly limited, and the layers may beproduced by any of a dry process and a wet process.

Specific examples of materials that can be used in the organicelectroluminescent device are shown below, but the materials that may beused in the invention are not construed as being limited to the examplecompounds. In some embodiments, a material having a particular functioncan also have another function.

In some embodiments, the host material is selected from the groupconsisting of:

Devices

In some embodiments, the compounds of the disclosure are incorporatedinto a device. For example, the device includes, but is not limited toan OLED bulb, an OLED lamp, a television screen, a computer monitor, amobile phone, and a tablet.

In some embodiments, an electronic device comprises an OLED comprisingan anode, a cathode, and at least one organic layer comprising alight-emitting layer between the anode and the cathode, wherein thelight-emitting layer comprises

-   -   a host material; and    -   a compound of Formula (I).

In some embodiments, the light-emitting layer of the OLED furthercomprises a fluorescent material wherein the compound of Formula (I)converts triplets to singlets for the fluorescent emitter.

In some embodiments, compositions described herein may be incorporatedinto various light-sensitive or light-activated devices, such as OLEDsor photovoltaic devices. In some embodiments, the composition may beuseful in facilitating charge transfer or energy transfer within adevice and/or as a hole-transport material. The device may be, forexample, an organic light-emitting diode (OLED), an organic integratedcircuit (O-IC), an organic field-effect transistor (O-FET), an organicthin-film transistor (O-TFT), an organic light-emitting transistor(O-LET), an organic solar cell (O-SC), an organic optical detector, anorganic photoreceptor, an organic field-quench device (O-FQD), alight-emitting electrochemical cell (LEC) or an organic laser diode(O-laser)

Bulbs or Lamps

In some embodiments, an electronic device comprises: an OLED comprisingan anode, a cathode, and at least one organic layer; and an OLED drivercircuit, the organic layer comprising a light-emitting layer between theanode and the cathode, wherein the light-emitting layer comprises:

-   -   a host material; and    -   a compound of Formula (I),    -   wherein the compound of Formula (I) is a light emitting        material.

In some embodiments, a device comprises OLEDs that differ in color. Insome embodiments, a device comprises an array comprising a combinationof OLEDs. In some embodiments, the combination of OLEDs is a combinationof three colors (e.g., RGB). In some embodiments, the combination ofOLEDs is a combination of colors that are not red, green, or blue (forexample, orange and yellow green). In some embodiments, the combinationof OLEDs is a combination of two, four, or more colors.

In some embodiments, a device is an OLED light comprising:

-   -   a circuit board having a first side with a mounting surface and        an opposing second side, and defining at least one aperture;    -   at least one MED on the mounting surface, the at least one OLED        configured to emanate light, comprising:        -   an anode, a cathode, and at least one organic layer            comprising a light-emitting layer between the anode and the            cathode, wherein the light-emitting layer comprises        -   a host material; and        -   a compound of Formula (I);        -   wherein the compound of Formula (I) is a light emitting            material;    -   a housing for the circuit board; and    -   at least one connector arranged at an end of the housing, the        housing and the connector defining a package adapted for        installation in a light fixture.

In some embodiments, the OLED light comprises a plurality of OLEDsmounted on a circuit board such that light emanates in a plurality ofdirections. In some embodiments, a portion of the light emanated in afirst direction is deflected to emanate in a second direction. In someembodiments, a reflector is used to deflect the light emanated in afirst direction.

Displays or Screens

In some embodiments, the compounds of Formula (I) can be used in ascreen or a display. In some embodiments, the compounds of Formula (I)are deposited onto a substrate using a process including, but notlimited to, vacuum evaporation, deposition, vapor deposition, orchemical vapor deposition (CVD). In some embodiments, the substrate is aphotoplate structure useful in a two-sided etch provides a unique aspectratio pixel. The screen (which may also be referred to as a mask) isused in a process in the manufacturing of OLED displays. Thecorresponding artwork pattern design facilitates a very steep and narrowtie-bar between the pixels in the vertical direction and a large,sweeping bevel opening in the horizontal direction. This allows theclose patterning of pixels needed for high definition displays whileoptimizing the chemical deposition onto a TFT backplane.

The internal patterning of the pixel allows the construction of a3-dimensional pixel opening with varying aspect ratios in the horizontaland vertical directions. Additionally, the use of imaged “stripes” orhalftone circles within the pixel area inhibits etching in specificareas until these specific patterns are undercut and fall off thesubstrate. At that point the entire pixel area is subjected to a similaretch rate, but the depths are varying depending on the halftone pattern.Varying the size and spacing of the halftone pattern allows etching tobe inhibited at different rates within the pixel allowing for alocalized deeper etch needed to create steep vertical bevels.

A preferred material for the deposition mask is invar. Invar is a metalalloy that is cold rolled into long thin sheet in a steel mill. Invarcannot be electrodeposited onto a rotating mandrel as the nickel mask. Apreferred and more cost feasible method for forming the open areas inthe mask used for deposition is through a wet chemical etching.

In some embodiments, a screen or display pattern is a pixel matrix on asubstrate. In some embodiments, a screen or display pattern isfabricated using lithography (e.g., photolithography and e-beamlithography). In some embodiments, a screen or display pattern isfabricated using a wet chemical etch. In further embodiments, a screenor display pattern is fabricated using plasma etching.

Methods of Manufacturing Devices Using the Disclosed Compounds

An OLED display is generally manufactured by forming a large motherpanel and then cutting the mother panel in units of cell panels. Ingeneral, each of the cell panels on the mother panel is formed byforming a thin film transistor (TFT) including an active layer and asource/drain electrode on a base substrate, applying a planarizationfilm to the TFT, and sequentially forming a pixel electrode, alight-emitting layer, a counter electrode, and an encapsulation layer,and then is cut from the mother panel.

An OLED display is generally manufactured by forming a large motherpanel and then cutting the mother panel in units of cell panels. Ingeneral, each of the cell panels on the mother panel is formed byforming a thin film transistor (TFT) including an active layer and asource/drain electrode on a base substrate, applying a planarizationfilm to the TFT, and sequentially forming a pixel electrode, alight-emitting layer, a counter electrode, and an encapsulation layer,and then is cut from the mother panel.

In another aspect, provided herein is a method of manufacturing anorganic light-emitting diode (OLED) display, the method comprising:

-   -   forming a barrier layer on a base substrate of a mother panel;    -   forming a plurality of display units in units of cell panels on        the barrier layer;    -   forming an encapsulation layer on each of the display units of        the cell panels; and    -   applying an organic film to an interface portion between the        cell panels.

In some embodiments, the barrier layer is an inorganic film formed of,for example, SiNx, and an edge portion of the barrier layer is coveredwith an organic film formed of polyimide or acryl. In some embodiments,the organic fain helps the mother panel to be softly cut in units of thecell panel.

In some embodiments, the thin film transistor (TFT) layer includes alight-emitting layer, a gate electrode, and a source/drain electrode.Each of the plurality of display units may include a thin filmtransistor (TFT) layer, a planarization film formed on the TFT layer,and a light-emitting unit formed on the planarization film, wherein theorganic film applied to the interface portion is formed of a samematerial as a material of the planarization film and is formed at a sametime as the planarization film is formed. In some embodiments, alight-emitting unit is connected to the TFT layer with a passivationlayer and a planarization film therebetween and an encapsulation layerthat covers and protects the light-emitting unit. In some embodiments ofthe method of manufacturing, the organic film contacts neither thedisplay units nor the encapsulation layer.

Each of the organic film and the planarization film may include any oneof polyimide and acryl. In some embodiments, the barrier layer may be aninorganic film. In some embodiments, the base substrate may be formed ofpolyimide. The method may further include, before the forming of thebarrier layer on one surface of the base substrate formed of polyimide,attaching a carrier substrate formed of a glass material to anothersurface of the base substrate, and before the cutting along theinterface portion, separating the carrier substrate from the basesubstrate. In some embodiments, the OLED display is a flexible display.

In some embodiments, the passivation layer is an organic film disposedon the TFT layer to cover the TFT layer. In some embodiments, theplanarization film is an organic film formed on the passivation layer.In some embodiments, the planarization film is formed of polyimide oracryl, like the organic film formed on the edge portion of the barrierlayer, In some embodiments, the planarization film and the organic filmare simultaneously formed when the OLED display is manufactured. In someembodiments, the organic film may he formed on the edge portion of thebarrier layer such that a portion of the organic film directly contactsthe base substrate and a remaining portion of the organic film contactsthe barrier layer while surrounding the edge portion of the barrierlayer.

In some embodiments, the light-emitting layer includes a pixelelectrode, a counter electrode, and an organic light-emitting layerdisposed between the pixel electrode and the counter electrode. In someembodiments, the pixel electrode is connected to the source/drainelectrode of the TFT layer.

In some embodiments, when a voltage is applied to the pixel electrodethrough the TFT layer, an appropriate voltage is formed between thepixel electrode and the counter electrode, and thus the organiclight-emitting layer emits light, thereby forming an image. Hereinafter,an image forming unit including the TFT layer and the light-emittingunit is referred to as a display unit.

In some embodiments, the encapsulation layer that covers the displayunit and prevents penetration of external moisture may be formed to havea thin film encapsulation structure in which an organic film and aninorganic film are alternately stacked. In some embodiments, theencapsulation layer has a thin film encapsulation structure in which aplurality of thin films are stacked. In some embodiments, the organicfilm applied to the interface portion is spaced apart from each of theplurality of display units. In some embodiments, the organic film isformed such that a portion of the organic film directly contacts thebase substrate and a remaining portion of the organic film contacts thebarrier layer while surrounding an edge portion of the barrier layer.

In one embodiment, the OLED display is flexible and uses the soft basesubstrate formed of polyimide. In some embodiments, the base substrateis formed on a carrier substrate formed of a glass material, and thenthe carrier substrate is separated.

In some embodiments, the barrier layer is formed on a surface of thebase substrate opposite to the carrier substrate. In one embodiment, thebarrier layer is patterned according to a size of each of the cellpanels. For example, while the base substrate is formed over the entiresurface of a mother panel, the barrier layer is formed according to asize of each of the cell panels, and thus a groove is formed at aninterface portion between the barrier layers of the cell panels. Each ofthe cell panels can be cut along the groove.

In some embodiments, the method of manufacture further comprises cuttingalong the interface portion, wherein a groove is formed in the barrierlayer, wherein at least a portion of the organic film is formed in thegroove, and wherein the groove does not penetrate into the basesubstrate. In some embodiments, the TFT layer of each of the cell panelsis formed, and the passivation layer which is an inorganic film and theplanarization film which is an organic film are disposed on the TFTlayer to cover the TFT layer. At the same time as the planarization filmthrilled of, for example, polyimide or acryl is formed, the groove atthe interface portion is covered with the organic film formed of, forexample, polyimide or acryl. This is to prevent cracks from occurring byallowing the organic film to absorb an impact generated when each of thecell panels is cut along the groove at the interface portion. That is,if the entire barrier layer is entirely exposed without the organicfilm, an impact generated when each of the cell panels is cut along thegroove at the interface portion is transferred to the barrier layer,thereby increasing the risk of cracks. However, in one embodiment, sincethe groove at the interface portion between the barrier layers iscovered with the organic film and the organic film absorbs an impactthat would otherwise he transferred to the barrier layer, each of thecell panels may be softly cut and cracks may be prevented from occurringin the barrier layer. In one embodiment, the organic film covering thegroove at the interface portion and the planarization film are spacedapart from each other. For example, if the organic film and theplanarization film are connected to each other as one layer, sinceexternal moisture may penetrate into the display unit through theplanarization film and a portion where the organic film remains, theorganic film and the planarization film are spaced apart from each othersuch that the organic film is spaced apart from the display unit.

In some embodiments, the display unit is formed by forming thelight-emitting unit, and the encapsulation layer is disposed on thedisplay unit to cover the display unit. As such, once the mother panelis completely manufactured, the carrier substrate that supports the basesubstrate is separated from the base substrate. In some embodiments,when a laser beam is emitted toward the carrier substrate, the carriersubstrate is separated from the base substrate due to a difference in athermal expansion coefficient between the carrier substrate and the basesubstrate.

In some embodiments, the mother panel is cut in units of the cellpanels. In some embodiments, the mother panel is cut along an interfaceportion between the cell panels by using a cutter. In some embodiments,since the groove at the interface portion along which the mother panelis cut is covered with the organic film, the organic film absorbs animpact during the cutting. In some embodiments, cracks may be preventedfrom occurring in the barrier layer during the cutting.

In some embodiments, the methods reduce a defect rate of a product andstabilize its quality.

Another aspect is an OLED display including: a barrier layer that isformed on a base substrate; a display unit that is formed on the barrierlayer; an encapsulation layer that is formed on the display unit; and anorganic film that is applied to an edge portion of the barrier layer.

All of the documents cited in this specification are expresslyincorporated by reference, in its entirety, into the presentapplication.

EXAMPLES

An embodiment of the present disclosure provides the preparation ofcompounds of Formula (I) according to the procedures of the followingexamples, using appropriate materials. Those skilled in the art willunderstand that known variations of the conditions and processes of thefollowing preparative procedures can be used to prepare these compounds.Moreover, by utilizing the procedures described in detail, one ofordinary skill in the art can prepare additional compounds of thepresent disclosure.

General Information on Analytical Methods

The features of the invention will be described more specifically withreference to examples below. The materials, processes, procedures andthe like shown below may be appropriately modified unless they deviatefrom the substance of the invention. Accordingly, the scope of theinvention is not construed as being limited to the specific examplesshown below. The characteristics of samples were evaluated by using NMR(Nuclear Magnetic Resonance 500 MHz, produced by Bruker), LC/MS (LiquidChromatography Mass Spectrometry, produced by Waters), AC3 (produced byRIKEN KEIKI), High-performance UV/Vis/NIR Spectrophotometer (Lambda 950,produced by PerkinElmer, Co., Ltd.), Fluorescence Spectrophotometer(FluoroMax-4, produced by Horiba, Ltd.), Photonic multichannel analyzer(PMA-12 C10027-01, produced by Hamamatsu Photonics K.K.), Absolute PLQuantum Yield Measurement System (C11347, produced by HamamatsuPhotonics K.K.), Automatic Current voltage brightness measurement system(ETS-170, produced by System engineers co ltd), Life Time

Measurement System (EAS-26C, produced by System engineers co ltd), andStreak Camera (Model C4334, produced by Hamamatsu Photonics K.K.).

Example 1

The principle of the features may be described as follows for an organicelectroluminescent device as an example.

In an organic electroluminescent device, carriers are injected from ananode and a cathode to a light-emitting material to form an excitedstate for the light-emitting material, with which light is emitted. Inthe case of a carrier injection type organic electroluminescent device,in general, excitons that are excited to the excited singlet state are25% of the total excitons generated, and the remaining 75% thereof areexcited to the excited triplet state. Accordingly, the use ofphosphorescence, which is light emission from the excited triplet state,provides a high energy utilization. However, the excited triplet statehas a long lifetime and thus causes saturation of the excited state anddeactivation of energy through mutual action with the excitons in theexcited triplet state, and therefore the quantum yield ofphosphorescence may generally he often not high. A delayed fluorescentmaterial emits fluorescent light through the mechanism that the energyof excitons transits to the excited triplet state through intersystemcrossing or the like, and then transits to the excited singlet statethrough reverse intersystem crossing due to triplet-triplet annihilationor absorption of thermal energy, thereby emitting fluorescent light. Itis considered that among the materials, a thermal activation typedelayed fluorescent material emitting light through absorption ofthermal energy is particularly useful for an organic electroluminescentdevice. In the case where a delayed fluorescent material is used in anorganic electroluminescent device, the excitons in the excited singletstate normally emit fluorescent light. On the other hand, the excitonsin the excited triplet state emit fluorescent light through intersystemcrossing to the excited singlet state by absorbing the heat generated bythe device. At this time, the light emitted through reverse intersystemcrossing from the excited triplet state to the excited singlet state hasthe same wavelength as fluorescent light since it is light emission fromthe excited singlet state, but has a longer lifetime (light emissionlifetime) than the normal fluorescent light and phosphorescent light,and thus the light is observed as fluorescent light that is delayed fromthe normal fluorescent light and phosphorescent light. The light may bedefined as delayed fluorescent light. The use of the thermal activationtype exciton transition mechanism may raise the proportion of thecompound in the excited singlet state, which is generally formed in aproportion only of 25%, to 25% or more through the absorption of thethermal energy after the carrier injection. A compound that emits strongfluorescent light and delayed fluorescent light at a low temperature oflower than 100° C. undergoes the intersystem crossing from the excitedtriplet state to the excited singlet state sufficiently with the heat ofthe device, thereby emitting delayed fluorescent light, and thus the useof the compound may drastically enhance the light emission efficiency.

Example 2

The compounds of the invention can be synthesized by any method known toone of ordinary skills in the art. The compounds are synthesized fromthe commonly available starting material. The various moieties can heassembled via linear or branched synthetic routes.

Synthesis of Compound 3

Compound 3 is obtained by stifling at 140° C. of a mixture of7-fluoro-2-oxo-2H-1-Benzopyran-3-carbonitrile 3a (1.0 g, 5.28 mmol),3,9′-Bi-9H-carbazole (1.93 g, 5.81 mmol) and K₂CO₃ (1.09 g, 7.89 mmol)in NMP (10 mL).

Synthesis of Compounds 19, 44, 79, 121, 175,185, 199, 234, 248, 280,302, 368, 397 and 410

Compounds 19, 44, 79, 121, 175,185, 199, 234, 248, 280, 302, 368, 397and 410 are obtained by changing the stating material and the reactantof the above process for Compound 3.

Example 3 Preparation of Neat Films

Each of the compounds synthesised in Example 2 is vapor-deposited on aquartz substrate by a vacuum vapor deposition method under a conditionof a vacuum degree of 10⁻³ Pa or less, so as to form a thin film havinga thickness of 70 nm.

Preparation of Doped Films

Each of the compounds synthesised in Example 2 and host arevapor-deposited from a separate vapor deposition source on a quartzsubstrate by vacuum vapor deposition method under a condition of avacuum degree of 10⁻³ Pa or less, so as to form a thin film having athickness of 100 nm and a concentration of the compound of 20% byweight.

Evaluation of the Optical Properties

The samples are irradiated with light having a wavelength of 300 nm at300 K, and thus the light emission spectrum is measured and designatedas fluorescence. The spectrum at 77K is also measured and designated asphosphorescence. The lowest singlet energy (S1) and the lowest tripletenergy (T1) are estimated from the onset of fluorescence andphosphorescence spectrum, respectively. ΔE_(ST) is calculated from theenergy gap between S1 and T1. PLQY is also measured by excitation light300 nm. The time resolved spectrum is obtained by excitation light 337nm with Streak Camera, and the component with a short light emissionlifetime is designated as fluorescent light, whereas the component witha long light emission lifetime is designated as delayed fluorescentlight. The lifetimes of the fluorescent light component (τ_(prompt)) andthe delayed fluorescent light component (τ_(delay)) are calculated fromthe decay curves.

Preparation and Measurement of OLEDs

Thin films are laminated on a glass substrate having formed thereon ananode formed of indium tin oxide (ITO) having a thickness of 50 nm, by avacuum vapor deposition method at a vacuum degree of 1.0×10⁻⁴ Pa orless. Firstly, HAT-CN is formed to a thickness of 60 nm on ITO, andthereon TrisPCz is formed to a thickness of 30 nm. mCBP is formed to athickness of 5 nm, and thereon compound of Formula (I) and host are thenvapor-co-deposited from separate vapor deposition sources to form alayer having thickness of 30 nm, which is designated as a light emittinglayer. At this time, the concentration of compound of Formula (I) is 20%by weight. SF3-TRZ is then formed to a thickness of 5 nm, and thereonSF3-TRZ and Liq are vapor-co-deposited to a thickness of 30 nm. Liq isthen vacuum vapor-deposited to a thickness of 2 nm, and then aluminum(Al) is vapor-deposited to a thickness of 100 nm to form a cathode,thereby producing organic electroluminescent devices and measured itsphotoelectrical properties.

Example 4

Q-Chem 5.1 program of Q-chem Inc. was used for calculation of thesynthesized compounds in Example 2. The B3LYP/6-31G(d) method was usedfor the optimization of the molecular structure of the S₀ state and itselectronic state calculation, and the time-dependent density functionaltheory (TD-DFT) method was used for S₁ and T₁ level calculation. ≢E_(ST)was obtained by calculating the difference between S₁ and T₁. Theresults are shown in the following table.

Compound No. Δ E_(ST) (eV) Compound 3 0.12 Compound 19 0.20 Compound 440.21 Compound 79 0.071 Compound 121 0.19 Compound 175 0.24 Compound 1850.22 Compound 199 0.18 Compound 234 0.023 Compound 248 0.053 Compound280 0.19 Compound 302 0.065 Compound 368 0.17 Compound 397 0.20 Compound410 0.030

We claim:
 1. A compound of Formula (I):

wherein: X is C(R)₂, O, S or —N(Ph), R is independently selected from H,CH₃, and Ph; Ph is substituted or unsubstituted phenyl, one of A¹ and A²is AA, AA is selected from CN, substituted or unsubstituted aryl havingat least one cyano, and substituted or unsubstituted heteroaryl havingat least one nitrogen atom as a ring-constituting atom, the other of A¹and A² is H, AA, substituted or unsubstituted alkyl, or substituted orunsubstituted aryl not haying cyano, one of D¹, D², D³ and D⁴ is DD, DDis represented by Formula (II):

R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are independently selected from hydrogen,deuterium, substituted or unsubstituted alkyl, substituted orunsubstituted alkoxy, substituted or unsubstituted amino, substituted orunsubstituted aryl, substituted or unsubstituted aryloxy, substituted orunsubstituted heteroaryl, substituted or unsubstituted heteroaryloxy,and silyl; or two or more instances of R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸taken together can form a ring system, or R⁵ and R⁶ taken together canform single bond, L¹ is selected from single bond, substituted orunsubstituted arylene, and substituted or unsubstituted heteroarylene;the others of D¹, D², D³ and D⁴ are selected from H, DD, substituted orunsubstituted alkyl, substituted or unsubstituted aryl other thanFormula (II).
 2. The compound of claim 1, wherein X is O.
 3. Thecompound of claim 1, wherein X is S.
 4. The compound of claim 1, whereinX is N(Ph).
 5. The compound of claim 4, wherein DD has two carbazolerings.
 6. The compound of claim 4, wherein at least one of D¹, D² and D⁴is DD.
 7. The compound of claim 4, wherein at least two of D¹, D², D³and D⁴ are DD.
 8. The compound of claim 4, wherein the at least two ofD¹, D², D³ and D⁴ are different from each other.
 9. The compound ofclaim 4, wherein R⁵ and R⁶ taken together form single bond, and R⁷ andR⁸ are not taken together.
 10. The compound of claim 4, wherein at leastone of D¹, D² and D⁴ is deuterium, substituted or unsubstituted alkyl,substituted or unsubstituted alkoxy, substituted or unsubstituted amino,substituted or unsubstituted aryl, substituted or unsubstituted aryloxy,substituted or unsubstituted heteroaryl, substituted or unsubstitutedheteroaryloxy, or silyl.
 11. The compound of claim 4, wherein at leastone of D¹, D² and D⁴ is substituted or unsubstituted amino, orsubstituted or unsubstituted heteroaryl.
 12. The compound of claim 4,wherein L¹ is substituted or unsubstituted arylene, and substituted orunsubstituted heteroarylene; wherein each instance of arylene andheteroarylene can be substituted with one or more substituentsindependently selected from deuterium, substituted or unsubstitutedalkyl, substituted or unsubstituted aryl, or substituted orunsubstituted heteroaryl.
 13. The compound of claim 4, wherein A¹ and A²are the same.
 14. The compound of claim 4, wherein A¹ and A² are AA anddifferent from each other.
 15. The compound of claim 4, wherein at leastone of A¹ and A² is substituted or unsubstituted aryl having at leastone cyano.
 16. An organic light-emitting diode (OLED) comprising thecompound of claim
 1. 17. The organic light-emitting diode (OLED) ofclaim 16, comprising an anode, a cathode, and at least one organic layercomprising a light-emitting layer between the anode and the cathode,wherein the light-emitting layer comprises a host material and thecompound.
 18. The organic light-emitting diode (OLED) of claim 16,comprising an anode, a cathode, and at least one organic layercomprising a light-emitting layer between the anode and the cathode,wherein the light-emitting layer comprises the compound and alight-emitting material, and light emission of the OLED occurs mainly inthe light-emitting material.
 19. The organic light-emitting diode (OLED)of claim 16, comprising an anode, a cathode, and at least one organiclayer comprising a light-emitting layer between the anode and thecathode, wherein the light-emitting layer comprises a host material, anassistant dopant and a light-emitting material, and the assistant dopantis the compound.
 20. A screen or a display comprising the compound ofclaim 1.